{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T01:53:01Z","timestamp":1760147581794,"version":"build-2065373602"},"reference-count":75,"publisher":"MDPI AG","issue":"4","license":[{"start":{"date-parts":[[2023,2,13]],"date-time":"2023-02-13T00:00:00Z","timestamp":1676246400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001809","name":"the National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["21971066","22171088","18JC1412300"],"award-info":[{"award-number":["21971066","22171088","18JC1412300"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003399","name":"the Science and Technology Commission of Shanghai Municipality","doi-asserted-by":"publisher","award":["21971066","22171088","18JC1412300"],"award-info":[{"award-number":["21971066","22171088","18JC1412300"]}],"id":[{"id":"10.13039\/501100003399","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The aromatic C(sp2)-H functionalization of unprotected naphthols with \u03b1-phenyl-\u03b1-diazoesters under mild conditions catalyzed by CuCl and CuCl2 exhibits high efficiency and unique ortho-selectivity. In this study, the combination of density functional theory (DFT) calculations and experiments is employed to investigate the mechanism of C-H functionalization, which reveals the fundamental origin of the site-selectivity. It explains that CuCl-catalyzed ortho-selective C-H functionlization is due to the bimetallic carbene, which differs from the reaction catalyzed by CuCl2 via monometallic carbene. The results demonstrate the function of favourable H-bond interactions on the site- and chemo-selectivity of reaction through stabilizing the rate-determining transition states in proton (1,3)-migration.<\/jats:p>","DOI":"10.3390\/molecules28041767","type":"journal-article","created":{"date-parts":[[2023,2,14]],"date-time":"2023-02-14T01:41:06Z","timestamp":1676338866000},"page":"1767","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Theoretical Study on the Copper-Catalyzed ortho-Selective C-H Functionalization of Naphthols with \u03b1-Phenyl-\u03b1-Diazoesters"],"prefix":"10.3390","volume":"28","author":[{"given":"Xiaoli","family":"Zhu","sequence":"first","affiliation":[{"name":"School of Chemistry and Molecular Engineering, East China Normal University, 500 Dongchuan Road, Shanghai 200241, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Xunshen","family":"Liu","sequence":"additional","affiliation":[{"name":"School of Chemistry and Molecular Engineering, East China Normal University, 500 Dongchuan Road, Shanghai 200241, China"},{"name":"Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, Shanghai 200062, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Fei","family":"Xia","sequence":"additional","affiliation":[{"name":"School of Chemistry and Molecular Engineering, East China Normal University, 500 Dongchuan Road, Shanghai 200241, China"},{"name":"NYU-ECNU Center for Computational Chemistry at New York University, East China Normal University, 3663 Zhongshan Road, Shanghai 200062, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2151-891X","authenticated-orcid":false,"given":"Lu","family":"Liu","sequence":"additional","affiliation":[{"name":"School of Chemistry and Molecular Engineering, East China Normal University, 500 Dongchuan Road, Shanghai 200241, China"},{"name":"Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, Shanghai 200062, China"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2023,2,13]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"919","DOI":"10.1021\/cr00075a013","article-title":"Catalytic Methods for Metal Carbene Transformations","volume":"86","author":"Doyle","year":"1986","journal-title":"Chem. Rev."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"3061","DOI":"10.1039\/b901170f","article-title":"Application of donor\/acceptor-carbenoids to the synthesis of natural products","volume":"38","author":"Davies","year":"2009","journal-title":"Chem. Soc. Rev."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"8186","DOI":"10.1002\/anie.200902785","article-title":"New syntheses of diazo compounds","volume":"48","author":"Maas","year":"2009","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"9981","DOI":"10.1021\/acs.chemrev.5b00121","article-title":"Modern Organic Synthesis with \u03b1-Diazocarbonyl Compounds","volume":"115","author":"Ford","year":"2015","journal-title":"Chem. Rev."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"506","DOI":"10.1039\/C5CS00821B","article-title":"Gold-catalyzed transformations of \u03b1-diazocarbonyl compounds: Selectivity and diversity","volume":"45","author":"Liu","year":"2016","journal-title":"Chem. Soc. Rev."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"908","DOI":"10.1039\/C9CS00542K","article-title":"Recent progress on donor and donor-donor carbenes","volume":"49","author":"Zhu","year":"2020","journal-title":"Chem. Soc. Rev."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"3872","DOI":"10.1002\/tcr.202100167","article-title":"Catalytic Functionalization of Metallocarbenes Derived from \u03b1-Diazocarbonyl Compounds and Their Precursors","volume":"21","author":"Yadagiri","year":"2021","journal-title":"Chem. Rec."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"2257","DOI":"10.1039\/C5CC08880A","article-title":"Gold-Catalyzed Construction of Two Adjacent Quaternary Stereocenters via Sequential C-H Functionalization and Aldol Annulation","volume":"52","author":"Yu","year":"2016","journal-title":"Chem. Commun."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"9351","DOI":"10.1039\/C6CC04034A","article-title":"Gold-catalysed facile access to indene scaffold via sequential C-H functionalization and 5-endo-dig carbocyclization","volume":"52","author":"Ma","year":"2016","journal-title":"Chem. Commun."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"10164","DOI":"10.1039\/C7CC05649D","article-title":"Gold-catalyzed para-selective C-H bond alkylation of benzene derivatives with donor\/acceptor-substituted diazo compounds","volume":"53","author":"Ma","year":"2017","journal-title":"Chem. Commun."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"8202","DOI":"10.1039\/D0CC01118E","article-title":"Gold-Catalyzed Intermolecular [4+1] Spiroannulation via Site Selective Aromatic C(sp2)-H Functionalization and Dearomatization of Phenol Derivatives","volume":"56","author":"Li","year":"2020","journal-title":"Chem. Commun."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"3770","DOI":"10.1039\/D1QO00276G","article-title":"Iron-catalysed chemo- and ortho-selective C-H bond functionalization of phenols with \u03b1-aryl-\u03b1-diazoacetates","volume":"8","author":"Yu","year":"2021","journal-title":"Org. Chem. Front."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"7298","DOI":"10.1038\/s41467-021-27167-x","article-title":"Modular and stereoselective synthesis of tetrasubstituted vinyl sulfides leading to a library of AIEgens","volume":"12","author":"Liu","year":"2021","journal-title":"Nat. Commun."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"2175","DOI":"10.1021\/acs.orglett.2c00477","article-title":"Highly Stereoselective Synthesis of Tetrasubstituted Vinyl Selenides via Rhodium-Catalyzed [1,4]-Acyl Migration of Selenoesters and Diazo Compounds","volume":"24","author":"Liu","year":"2022","journal-title":"Org. Lett."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"e202208874","DOI":"10.1002\/anie.202208874","article-title":"Enantioselective para-C(sp2)-H Functionalization of Alkyl Benzene Derivatives via Cooperative Catalysis of Gold\/Chiral Br\u00f8nsted Acid","volume":"61","author":"Liu","year":"2022","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"385","DOI":"10.1016\/j.gresc.2021.10.001","article-title":"Borane-catalysed S\u2013H insertion reaction of thiophenols and thiols with \u03b1-aryl-\u03b1-diazoesters","volume":"2","author":"Dong","year":"2021","journal-title":"Green Synth. Catal."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"183","DOI":"10.1039\/b309046a","article-title":"Ruthenium-catalysed carbenoid cyclopropanation reactions with diazo compounds","volume":"33","author":"Maas","year":"2004","journal-title":"Chem. Soc. Rev."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"1471","DOI":"10.1126\/science.1218781","article-title":"Iron-catalyzed cyclopropanation in 6M KOH with in situ generation of diazomethane","volume":"335","author":"Morandi","year":"2012","journal-title":"Science"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"2861","DOI":"10.1021\/cr0200217","article-title":"Catalytic enantioselective C-H activation by means of metal-carbenoid-induced C-H insertion","volume":"103","author":"Davies","year":"2003","journal-title":"Chem. Rev."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"417","DOI":"10.1038\/nature06485","article-title":"Catalytic C-H functionalization by metal carbenoid and nitrenoid insertion","volume":"451","author":"Davies","year":"2008","journal-title":"Nature"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"3379","DOI":"10.1021\/cr078364y","article-title":"Coinage metal catalyzed C-H bond functionalization of hydrocarbons","volume":"108","author":"Perez","year":"2008","journal-title":"Chem. Rev."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"704","DOI":"10.1021\/cr900239n","article-title":"Catalytic carbene insertion into C-H bonds","volume":"110","author":"Doyle","year":"2010","journal-title":"Chem. Rev."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"4740","DOI":"10.1039\/c1cs15083a","article-title":"Towards mild metal-catalyzed C-H bond activation","volume":"40","author":"Droge","year":"2011","journal-title":"Chem. Soc. Rev."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"6173","DOI":"10.1039\/c3ra46996d","article-title":"Recent development of direct asymmetric functionalization of inert C\u2013H bonds","volume":"4","author":"Zheng","year":"2014","journal-title":"RSC Adv."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"5879","DOI":"10.1021\/cr300153j","article-title":"Ruthenium(II)-catalyzed C-H bond activation and functionalization","volume":"112","author":"Arockiam","year":"2012","journal-title":"Chem. Rev."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"2015","DOI":"10.1002\/ajoc.201800472","article-title":"Gold-Catalyzed Site-Selective C\u2212H Bond Functionalization with Diazo Compounds","volume":"7","author":"Ma","year":"2018","journal-title":"Asian J. Org. Chem."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"2749","DOI":"10.1002\/anie.201611809","article-title":"Highly para-selective C-H Alkylation of Benzene Derivatives with 2,2,2-Trifluoroethyl \u03b1-Aryl-\u03b1-diazoesters","volume":"56","author":"Ma","year":"2017","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"6916","DOI":"10.1039\/D1QO01265G","article-title":"Catalyst-free synthesis of \u03b1,\u03b1-disubstituted carboxylic acid derivatives under ambient conditions via a Wolff rearrangement reaction","volume":"8","author":"Ji","year":"2021","journal-title":"Org. Chem. Front."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"6444","DOI":"10.1021\/acs.orglett.8b02757","article-title":"Phosphine-Catalyzed [3+2] Cycloaddition reaction of \u03b1-Diazoacetates and \u03b2-Trifluoromethyl Enones: A Facile Access to Multisubstituted 4-CF3 Pyrazolines","volume":"20","author":"Li","year":"2018","journal-title":"Org. Lett."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"4918","DOI":"10.1039\/c3cs35496b","article-title":"Catalytic X-H insertion reactions based on carbenoids","volume":"42","author":"Gillingham","year":"2013","journal-title":"Chem. Soc. Rev."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"14191","DOI":"10.1002\/anie.201408335","article-title":"Rhodium-catalyzed NH insertion of pyridyl carbenes derived from pyridotriazoles: A general and efficient approach to 2-picolylamines and imidazo[1,5-a]pyridines","volume":"53","author":"Shi","year":"2014","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"2450","DOI":"10.1002\/anie.201006139","article-title":"Removable directing groups in organic synthesis and catalysis","volume":"50","author":"Rousseau","year":"2011","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"7325","DOI":"10.1021\/ja302710v","article-title":"Dehydrative C-H Alkylation and Alkenylation of Phenols with Alcohols: Expedient Synthesis for Substituted Phenols and Benzofurans","volume":"134","author":"Lee","year":"2012","journal-title":"J. Am. Chem. Soc."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"7710","DOI":"10.1002\/anie.201403894","article-title":"Direct functionalization with complete and switchable positional control: Free phenol as a role model","volume":"53","author":"Yu","year":"2014","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"12390","DOI":"10.1021\/jacs.7b06785","article-title":"Cu(II)-Catalyzed ortho-Selective Aminomethylation of Phenols","volume":"139","author":"Dai","year":"2017","journal-title":"J. Am. Chem. Soc."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"521","DOI":"10.1021\/acscatal.8b04098","article-title":"Phenol-Directed C\u2013H Functionalization","volume":"9","author":"Huang","year":"2018","journal-title":"ACS Catal."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"11807","DOI":"10.1002\/anie.201804829","article-title":"Cu-Catalyzed Cross-Dehydrogenative ortho-Aminomethylation of Phenols","volume":"57","author":"Yu","year":"2018","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"3441","DOI":"10.1021\/acs.orglett.9b01214","article-title":"Rhenium-Catalyzed Regioselective ortho-Alkenylation and [3+2+1] Cycloaddition of Phenols with Internal Alkynes","volume":"21","author":"Murai","year":"2019","journal-title":"Org. Lett."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"10811","DOI":"10.1016\/0040-4020(95)00648-R","article-title":"Synthetic applications of the O-H insertion reactions of carbenes and carbenoids derived from diazocarbonyl and related diazo compounds","volume":"51","author":"Miller","year":"1995","journal-title":"Tetrahedron"},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"1365","DOI":"10.1021\/ar300051u","article-title":"Transition-metal-catalyzed enantioselective heteroatom-hydrogen bond insertion reactions","volume":"45","author":"Zhu","year":"2012","journal-title":"Acc. Chem. Res."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"2427","DOI":"10.1021\/ar300340k","article-title":"Novel multicomponent reactions via trapping of protic onium ylides with electrophiles","volume":"46","author":"Guo","year":"2013","journal-title":"Acc. Chem. Res."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"2978","DOI":"10.1002\/anie.201309820","article-title":"Enantioselective palladium-catalyzed insertion of \u03b1-aryl-\u03b1-diazoacetates into the O-H bonds of phenols","volume":"53","author":"Xie","year":"2014","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"11956","DOI":"10.1002\/anie.201504483","article-title":"Enantioselective palladium-catalyzed C-H functionalization of indoles using an axially chiral 2,2\u2032-bipyridine metal","volume":"54","author":"Gao","year":"2015","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"2754","DOI":"10.1002\/adsc.201700572","article-title":"Rhodium(II)\/Chiral Phosphoric Acid-Cocatalyzed Enantioselective O-H Bond Insertion of \u03b1-Diazo Esters","volume":"359","author":"Zhang","year":"2017","journal-title":"Adv. Synth. Catal."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"6904","DOI":"10.1021\/ja503163k","article-title":"Highly site-selective direct C-H bond functionalization of phenols with \u03b1-aryl-\u03b1-diazoacetates and diazooxindoles via gold catalysis","volume":"136","author":"Yu","year":"2014","journal-title":"J. Am. Chem. Soc."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"14807","DOI":"10.1002\/anie.201608937","article-title":"B(C6F5)3 Catalyzed Chemoselective and ortho-Selective Substitution of Phenols with \u03b1-Aryl \u03b1-Diazoesters","volume":"55","author":"Yu","year":"2016","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"6553","DOI":"10.1039\/C9SC01657K","article-title":"Ligand and counteranion enabled regiodivergent C-H bond functionalization of naphthols with \u03b1-aryl-\u03b1-diazoesters","volume":"10","author":"Yu","year":"2019","journal-title":"Chem. Sci."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"3650","DOI":"10.1016\/j.tet.2019.05.040","article-title":"Gold-catalyzed chemoselective formal (3\u00fe2)-Annulation reaction between \u03b2-naphthols and methyl aryldiazoacetate","volume":"75","author":"Harada","year":"2019","journal-title":"Tetrahedron"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"3464","DOI":"10.1039\/c2cs15323h","article-title":"Recent advances in copper-catalyzed dehydrogenative functionalization via a single electron transfer (SET) process","volume":"41","author":"Zhang","year":"2012","journal-title":"Chem. Soc. Rev."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"10162","DOI":"10.1039\/c2cc34406h","article-title":"Recent developments in copper-catalyzed reactions of diazo compounds","volume":"48","author":"Zhao","year":"2012","journal-title":"Chem. Commun."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"1622","DOI":"10.1021\/cr500410y","article-title":"Copper-catalyzed C-H functionalization reactions: Efficient synthesis of heterocycles","volume":"115","author":"Guo","year":"2015","journal-title":"Chem. Rev."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"4504","DOI":"10.1039\/C5CS00882D","article-title":"Copper-catalyzed oxidative carbon-heteroatom bond formation: A recent update","volume":"45","author":"Zhu","year":"2016","journal-title":"Chem. Soc. Rev."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"967","DOI":"10.1021\/acscatal.0c04618","article-title":"Recent Advances in Copper Promoted Inert C(sp3)\u2013H Functionalization","volume":"11","author":"Yang","year":"2021","journal-title":"ACS Catal."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"5376","DOI":"10.1021\/ja01141a047","article-title":"The Copper-Catalyzed Decomposition of Diazoketones","volume":"74","author":"Yates","year":"1952","journal-title":"J. Am. Chem. Soc."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"4594","DOI":"10.1021\/ja0607739","article-title":"Catalytic enantioselective O-H insertion reactions","volume":"128","author":"Maier","year":"2006","journal-title":"J. Am. Chem. Soc."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"12616","DOI":"10.1021\/ja074729k","article-title":"Highly enantioselective insertion of carbenoids into O-H bonds of phenols: An efficient approach to chiral \u03b1-aryloxycarboxylic esters","volume":"129","author":"Chen","year":"2007","journal-title":"J. Am. Chem. Soc."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"2555","DOI":"10.1002\/anie.201209455","article-title":"Enantioselective copper-catalyzed intramolecular phenolic O-H bond insertion: Synthesis of chiral 2-carboxy dihydrobenzofurans, dihydrobenzopyrans, and tetrahydrobenzooxepines","volume":"52","author":"Song","year":"2013","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"2914","DOI":"10.1021\/om030243a","article-title":"Copper-catalyzed carbene insertion into O-H bonds: High selective conversion of alcohols into ethers","volume":"22","author":"Morilla","year":"2003","journal-title":"Organometallics"},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"17783","DOI":"10.1021\/ja9086566","article-title":"Why is copper(I) complex more competent than dirhodium(II) complex in catalytic asymmetric O-H insertion reactions? A computational study of the metal carbenoid O-H insertion into water","volume":"131","author":"Liang","year":"2009","journal-title":"J. Am. Chem. Soc."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"5491","DOI":"10.1039\/c3ob40941d","article-title":"Combined C-H functionalization\/O-H insertion reaction to form tertiary \u03b2-alkoxy substituted \u03b2-aminophosphonates catalyzed by [Cu(MeCN)4]PF6","volume":"11","author":"Cai","year":"2013","journal-title":"Org. Biomol. Chem."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"6485","DOI":"10.1021\/acs.jpca.6b05735","article-title":"DFT Calculations on the Mechanism of Transition-Metal-Catalyzed Reaction of Diazo Compounds with Phenols: O-H Insertion versus C-H Insertion","volume":"120","author":"Liu","year":"2016","journal-title":"J. Phys. Chem. A"},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"1988","DOI":"10.1039\/C5SC04319K","article-title":"Origins of unique gold-catalysed chemo- and site-selective C-H functionalization of phenols with diazo compounds","volume":"7","author":"Liu","year":"2016","journal-title":"Chem. Sci."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"9485","DOI":"10.1039\/D0CC04495D","article-title":"Copper-catalysed ortho-selective C-H bond functionalization of phenols and naphthols with \u03b1-aryl-\u03b1-diazoesters","volume":"56","author":"Ma","year":"2020","journal-title":"Chem. Commun."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"2029","DOI":"10.1021\/acs.jpca.9b11991","article-title":"How CuCl and CuCl2 Insert into C-N Bonds of Diazo Compounds: An Electronic Structure and Mechanistic Study","volume":"124","author":"Li","year":"2020","journal-title":"J. Phys. Chem. A"},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"5284","DOI":"10.1002\/anie.200501056","article-title":"A gold catalyst for carbene-transfer reactions from ethyl diazoacetate","volume":"44","author":"Fructos","year":"2005","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"1573","DOI":"10.1002\/chem.201203217","article-title":"Reactivity of stabilized vinyl diazo derivatives toward unsaturated hydrocarbons: Regioselective gold-catalyzed carbon-carbon bond formation","volume":"19","author":"Barluenga","year":"2013","journal-title":"Chem. Eur. J."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"1925","DOI":"10.1021\/acs.jpca.6b00636","article-title":"Mechanistic Investigation of Aromatic C(sp2)-H and Alkyl C(sp3)-H Bond Insertion by Gold Carbenes","volume":"120","author":"Liu","year":"2016","journal-title":"J. Phys. Chem. A"},{"key":"ref_68","unstructured":"Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., and Petersson, G.A. (2010). Gaussian 09, Revision B.01, Gaussian, Inc."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"6615","DOI":"10.1039\/b810189b","article-title":"Long-range corrected hybrid density functionals with damped atom-atom dispersion corrections","volume":"10","author":"Chai","year":"2008","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"084107","DOI":"10.1063\/1.3545971","article-title":"Density-functional approaches to noncovalent interactions: A comparison of dispersion corrections (DFT-D), exchange-hole dipole moment (XDM) theory, and specialized functionals","volume":"134","author":"Burns","year":"2011","journal-title":"J. Chem. Phys."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"866","DOI":"10.1063\/1.452288","article-title":"Energy-adjusted ab initio pseudopotentials for the first row transition elements","volume":"86","author":"Dolg","year":"1987","journal-title":"J. Chem. Phys."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"2257","DOI":"10.1063\/1.1677527","article-title":"Self-Consistent Molecular Orbital Methods. XII. Further Extensions of Gaussian-Type Basis Sets for Use in Molecular Orbital Studies of Organic Molecules","volume":"56","author":"Hehre","year":"1972","journal-title":"J. Chem. Phys."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"4161","DOI":"10.1021\/j100717a029","article-title":"A Formulation of the reaction coordinate","volume":"74","author":"Fukui","year":"1970","journal-title":"J. Phys. Chem."},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"363","DOI":"10.1021\/ar00072a001","article-title":"The path of chemical reactions-the IRC approach","volume":"14","author":"Fukui","year":"1981","journal-title":"Acc. Chem. Res."},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"6378","DOI":"10.1021\/jp810292n","article-title":"Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions","volume":"113","author":"Marenich","year":"2009","journal-title":"J. Phys. Chem. B"}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/4\/1767\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T18:33:44Z","timestamp":1760121224000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/4\/1767"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,2,13]]},"references-count":75,"journal-issue":{"issue":"4","published-online":{"date-parts":[[2023,2]]}},"alternative-id":["molecules28041767"],"URL":"https:\/\/doi.org\/10.3390\/molecules28041767","relation":{},"ISSN":["1420-3049"],"issn-type":[{"type":"electronic","value":"1420-3049"}],"subject":[],"published":{"date-parts":[[2023,2,13]]}}}