{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,30]],"date-time":"2026-09-30T02:35:31Z","timestamp":1790735731533,"version":"4.1.0"},"reference-count":46,"publisher":"MDPI AG","issue":"12","license":[{"start":{"date-parts":[[2022,6,9]],"date-time":"2022-06-09T00:00:00Z","timestamp":1654732800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["22001089"],"award-info":[{"award-number":["22001089"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["BK20191046"],"award-info":[{"award-number":["BK20191046"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["SF201505"],"award-info":[{"award-number":["SF201505"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Natural Science Foundation of Jiangsu Province","award":["22001089"],"award-info":[{"award-number":["22001089"]}]},{"name":"Natural Science Foundation of Jiangsu Province","award":["BK20191046"],"award-info":[{"award-number":["BK20191046"]}]},{"name":"Natural Science Foundation of Jiangsu Province","award":["SF201505"],"award-info":[{"award-number":["SF201505"]}]},{"name":"Opening Funding of Jiangsu Provincial Engineering Laboratory for Advanced Materials of Salt Chemical Industry","award":["22001089"],"award-info":[{"award-number":["22001089"]}]},{"name":"Opening Funding of Jiangsu Provincial Engineering Laboratory for Advanced Materials of Salt Chemical Industry","award":["BK20191046"],"award-info":[{"award-number":["BK20191046"]}]},{"name":"Opening Funding of Jiangsu Provincial Engineering Laboratory for Advanced Materials of Salt Chemical Industry","award":["SF201505"],"award-info":[{"award-number":["SF201505"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>An efficient and practical catalytic system for the oxidation of alcohols to aldehydes\/ketones using catalytic amounts of Bi(NO3)3 and Keto-ABNO (9-azabicyclo [3.3.1]nonan-3-one N-oxyl) with air as the environmentally benign oxidant was developed. Various primary and secondary alcohols were smoothly oxidized to the corresponding products under mild conditions, and satisfactory yields were achieved. Moreover, this methodology avoids the use of a ligand and base. The gram-scale reaction was demonstrated for the oxidation of 1-phenyl ethanol, and the product of acetophenone was obtained at an isolated yield of about 94%.<\/jats:p>","DOI":"10.3390\/molecules27123727","type":"journal-article","created":{"date-parts":[[2022,6,12]],"date-time":"2022-06-12T22:37:20Z","timestamp":1655073440000},"page":"3727","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":13,"title":["A Highly Efficient Bismuth Nitrate\/Keto-ABNO Catalyst System for Aerobic Oxidation of Alcohols to Carbonyl Compounds under Mild Conditions"],"prefix":"10.3390","volume":"27","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-6378-1404","authenticated-orcid":false,"given":"Yongke","family":"Hu","sequence":"first","affiliation":[{"name":"National & Local Joint Engineering Research Center for Mineral Salt Deep Utilization, Huaiyin Institute of Technology, Huaian 223003, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lei","family":"Chen","sequence":"additional","affiliation":[{"name":"Zhongbei College, Nanjing Normal University, Zhenjiang 212300, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Gulou","family":"Shen","sequence":"additional","affiliation":[{"name":"National & Local Joint Engineering Research Center for Mineral Salt Deep Utilization, Huaiyin Institute of Technology, Huaian 223003, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jin","family":"Li","sequence":"additional","affiliation":[{"name":"National & Local Joint Engineering Research Center for Mineral Salt Deep Utilization, Huaiyin Institute of Technology, Huaian 223003, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shaozhong","family":"Li","sequence":"additional","affiliation":[{"name":"National & Local Joint Engineering Research Center for Mineral Salt Deep Utilization, Huaiyin Institute of Technology, Huaian 223003, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Huaju","family":"Li","sequence":"additional","affiliation":[{"name":"National & Local Joint Engineering Research Center for Mineral Salt Deep Utilization, Huaiyin Institute of Technology, Huaian 223003, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yanxing","family":"Li","sequence":"additional","affiliation":[{"name":"National & Local Joint Engineering Research Center for Mineral Salt Deep Utilization, Huaiyin Institute of Technology, Huaian 223003, China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2022,6,9]]},"reference":[{"key":"ref_1","unstructured":"Hudlicky, M. (1990). Oxidations in Organic Chemistry, American Chemical Society."},{"key":"ref_2","unstructured":"Tojo, G., and Fern\u00e1ndez, M.I. (2006). Oxidation of Alcohols to Aldehydes and Ketones: A Guide to Current Common Practice, Springer Science & Business Media."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"774","DOI":"10.1021\/ar010075n","article-title":"Green, Catalytic Oxidations of Alcohols","volume":"35","author":"Sheldon","year":"2002","journal-title":"Acc. Chem. Res."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"851","DOI":"10.1021\/ar050113t","article-title":"Tandem oxidation processes using manganese dioxide: Discovery, applications, and current studies","volume":"38","author":"Taylor","year":"2005","journal-title":"Acc. Chem. Res."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"1039","DOI":"10.1021\/jo052137j","article-title":"Oxidation of alcohols to carbonyl compounds with CrO3\u00b7SiO2 in supercritical carbon dioxide","volume":"71","author":"Mello","year":"2006","journal-title":"J. Org. Chem."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"6895","DOI":"10.1016\/j.tetlet.2014.10.100","article-title":"Activation of DMSO for Swern-type oxidation by 1,1-dichlorocycloheptatriene","volume":"55","author":"Nguyen","year":"2014","journal-title":"Tetrahedron Lett."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"3017","DOI":"10.1016\/j.tetlet.2007.02.123","article-title":"I2O5: Mild and efficient reagents for the oxidation of alcohols in water","volume":"48","author":"Liu","year":"2007","journal-title":"Tetrahedron Lett."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"2329","DOI":"10.1021\/cr050523v","article-title":"Recent advances in transition metal catalyzed oxidation of organic substrates with molecular oxygen","volume":"105","author":"Punniyamurthy","year":"2005","journal-title":"Chem. Rev."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"3381","DOI":"10.1039\/c2cs15224j","article-title":"Recent advances in transition-metal catalyzed reactions using molecular oxygen as the oxidant","volume":"41","author":"Shi","year":"2012","journal-title":"Chem. Soc. Rev."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"3928","DOI":"10.1021\/acs.orglett.1c01058","article-title":"SBA-15 Supported 1-Methyl-2-azaadamanane N-Oxyl (1-Me-AZADO) as Recyclable Catalyst for Oxidation of Alcohol","volume":"23","author":"Tian","year":"2021","journal-title":"Org. Lett."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"2722","DOI":"10.1016\/j.tetlet.2018.05.071","article-title":"HKUST-1\/ABNO-catalyzed aerobic oxidation of secondary benzyl alcohols at room temperature","volume":"59","author":"Kim","year":"2018","journal-title":"Tetrahedron Lett."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"2189","DOI":"10.1021\/acs.joc.6b00009","article-title":"Iron\/ABNO-Catalyzed Aerobic Oxidation of Alcohols to Aldehydes and Ketones under Ambient Atmosphere","volume":"81","author":"Wang","year":"2016","journal-title":"J. Org. Chem."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"3101","DOI":"10.1039\/C9QO00740G","article-title":"Copper catalysis for highly selective aerobic oxidation of alcohols to aldehydes\/ketones","volume":"6","author":"Zhai","year":"2019","journal-title":"Org. Chem. Front."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"3400","DOI":"10.1002\/anie.200300630","article-title":"Palladium oxidase catalysis: Selective oxidation of organic chemicals by direct dioxygen-coupled turnover","volume":"43","author":"Stahl","year":"2004","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"2369","DOI":"10.1021\/ol0260977","article-title":"[RuCl2(p-cymene)]2 on carbon: An efficient, selective, reusable, and environmentally versatile heterogeneous catalyst","volume":"4","author":"Choi","year":"2002","journal-title":"Org. Lett."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"825","DOI":"10.1021\/ar4001907","article-title":"The important role of hydroxyl on oxidation catalysis by gold nanoparticles","volume":"47","author":"Ide","year":"2014","journal-title":"Acc. Chem. Res."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"54","DOI":"10.1021\/ol5032156","article-title":"Highly efficient oxidation of secondary alcohols to ketones catalyzed by manganese complexes of N4 ligands with H2O2","volume":"17","author":"Shen","year":"2015","journal-title":"Org. Lett."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"4605","DOI":"10.1039\/C6GC01272H","article-title":"Acceptorless dehydrogenation and aerobic oxidation of alcohols with a reusable binuclear rhodium(II) catalyst in water","volume":"18","author":"Wang","year":"2016","journal-title":"Green Chem."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"2070","DOI":"10.1016\/j.tetlet.2012.02.033","article-title":"Oxidation of nitroxyl radicals: Electrochemical and computational studies","volume":"53","author":"Shibuya","year":"2012","journal-title":"Tetrahedron Lett."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"4524","DOI":"10.1039\/C3CC47081D","article-title":"Aerobic oxidation catalysis with stable radicals","volume":"50","author":"Cao","year":"2014","journal-title":"Chem. Commun."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"8027","DOI":"10.1021\/acs.joc.1c00410","article-title":"TEMPO-Functionalized Nanoreactors from Bottlebrush Copolymers for the Selective Oxidation of Alcohols in Water","volume":"86","author":"Wang","year":"2021","journal-title":"J. Org. Chem."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"11184","DOI":"10.1021\/acs.joc.5b01950","article-title":"Stable TEMPO and ABNO Catalyst Solutions for User-Friendly (bpy)Cu\/Nitroxyl-Catalyzed Aerobic Alcohol Oxidation","volume":"80","author":"Steves","year":"2015","journal-title":"J. Org. Chem."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"4649","DOI":"10.1039\/c0cs00206b","article-title":"Applications of bismuth(III) compounds in organic synthesis","volume":"40","author":"Bothwell","year":"2011","journal-title":"Chem. Soc. Rev."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"1382","DOI":"10.1021\/acscatal.1c04897","article-title":"Bismuth Redox Catalysis: An Emerging Main-Group Platform for Organic Synthesis","volume":"12","author":"Moon","year":"2022","journal-title":"ACS Catal."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"983","DOI":"10.1016\/j.cclet.2015.04.012","article-title":"Facile one-pot clean synthesis of benzimidazole motifs: Exploration on bismuth nitrate accelerated subtle catalysis","volume":"26","author":"Mahire","year":"2015","journal-title":"Chin. Chem. Lett."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"5001","DOI":"10.1039\/D1DT00158B","article-title":"The room temperature synthesis of a CuO-Bi-BiOBr ternary Z-scheme photocatalyst for enhanced sunlight driven alcohol oxidation","volume":"50","author":"Bisht","year":"2021","journal-title":"Dalton Trans."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"3776","DOI":"10.1002\/celc.202000911","article-title":"Nitrate Radical Facilitates Indirect Benzyl Alcohol Oxidation on Bismuth(III) Vanadate Photoelectrodes","volume":"7","author":"Terry","year":"2020","journal-title":"ChemElectroChem"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"5072","DOI":"10.1021\/ol402428e","article-title":"Aerobic oxidation of diverse primary alcohols to methyl esters with a readily accessible heterogeneous Pd\/Bi\/Te catalyst","volume":"15","author":"Powell","year":"2013","journal-title":"Org. Lett."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"7301","DOI":"10.1016\/j.tet.2017.11.025","article-title":"Efficient and selective palladium-catalyzed direct oxidative esterification of benzylic alcohols under aerobic conditions","volume":"73","author":"Hu","year":"2017","journal-title":"Tetrahedron"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"3736","DOI":"10.1055\/s-0030-1258221","article-title":"Bismuth(III) Oxide Catalyzed Oxidation of Alcohols with tert-Butyl Hydroperoxide","volume":"2010","author":"Chakraborty","year":"2010","journal-title":"Synthesis"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"2434","DOI":"10.1055\/s-0035-1560467","article-title":"Bismuth Tribromide Catalyzed Oxidation of Alcohols with Aqueous Hydrogen Peroxide","volume":"26","author":"Lee","year":"2015","journal-title":"Synlett"},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"570","DOI":"10.1016\/j.tetlet.2019.01.034","article-title":"Aerobic oxidation of alcohols using bismuth bromide as a catalyst","volume":"60","author":"Ueno","year":"2019","journal-title":"Tetrahedron Lett."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"2588","DOI":"10.1016\/j.catcom.2008.07.019","article-title":"Bismuth(III) nitrate pentahydrate: A stoichiometric reagent for microwave induced mild and highly efficient aerial oxidation of aromatic aldehydes under solvent-free conditions","volume":"9","author":"Mukhopadhyay","year":"2008","journal-title":"Catal. Commun."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"9","DOI":"10.1016\/j.catcom.2016.01.003","article-title":"Bi(NO3)3\u00b75H2O and cellulose mediated Cu-NPs\u2014A highly efficient and novel catalytic system for aerobic oxidation of alcohols to carbonyls and synthesis of DFF from HMF","volume":"77","author":"Baruah","year":"2016","journal-title":"Catal. Commun."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"82","DOI":"10.1016\/j.catcom.2016.05.017","article-title":"NHPI\/tert-butyl nitrite: A highly efficient metal-free catalytic system for aerobic oxidation of alcohols to carbonyl compounds using molecular oxygen as the terminal oxidant","volume":"83","author":"Hu","year":"2016","journal-title":"Catal. Commun."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"2744","DOI":"10.1039\/C9QO00657E","article-title":"Copper-catalyzed tandem oxidative synthesis of quinazolinones from 2-aminobenzonitriles and benzyl alcohols","volume":"6","author":"Hu","year":"2019","journal-title":"Org. Chem. Front."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"65196","DOI":"10.1039\/C6RA12164K","article-title":"Iron nitrate\/TEMPO-catalyzed aerobic oxidative synthesis of quinazolinones from alcohols and 2-aminobenzamides with air as the oxidant","volume":"6","author":"Hu","year":"2016","journal-title":"RSC Adv."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"7308","DOI":"10.1007\/s10853-020-05726-9","article-title":"Direct oxidative esterification of alcohols catalyzed by a nitrogen-doped carbon black-supported PdBi bimetallic catalyst under ambient conditions","volume":"56","author":"Hu","year":"2021","journal-title":"J. Mater. Sci."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"464","DOI":"10.1016\/j.cclet.2017.10.036","article-title":"Practical CuCl\/DABCO\/4-HO-TEMPO-catalyzed oxidative synthesis of nitriles from alcohols with air as oxidant","volume":"29","author":"Hu","year":"2018","journal-title":"Chin. Chem. Lett."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"1720","DOI":"10.1039\/C4CY00219A","article-title":"Copper(I)\/ketoABNO catalysed aerobic alcohol oxidation","volume":"4","author":"Rogan","year":"2014","journal-title":"Catal. Sci. Technol."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"2735","DOI":"10.1002\/cssc.201402059","article-title":"SBA-15-Functionalized 3-Oxo-ABNO as Recyclable Catalyst for Aerobic Oxidation of Alcohols under Metal-Free Conditions","volume":"7","author":"Karimi","year":"2014","journal-title":"ChemSusChem"},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"652","DOI":"10.1016\/j.tetlet.2017.01.012","article-title":"Aerobic oxidation of secondary alcohols in water with ABNO\/tert-butyl nitrite\/KPF6 catalytic system","volume":"58","author":"Ma","year":"2017","journal-title":"Tetrahedron Lett."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"1259","DOI":"10.1002\/adsc.201801499","article-title":"Europium-Catalyzed Aerobic Oxidation of Alcohols to Aldehydes\/Ketones and Photoluminescence Tracking","volume":"361","author":"Kim","year":"2019","journal-title":"Adv. Synth. Catal."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"3675","DOI":"10.1016\/j.tet.2004.02.046","article-title":"Bismuth compounds in organic synthesis. Bismuth nitrate catalyzed chemoselective synthesis of acylals from aromatic aldehydes","volume":"60","author":"Aggen","year":"2004","journal-title":"Tetrahedron"},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"1005","DOI":"10.1002\/adsc.201100033","article-title":"Development of a General and Practical Iron Nitrate\/TEMPO-Catalyzed Aerobic Oxidation of Alcohols to Aldehydes\/Ketones: Catalysis with Table Salt","volume":"353","author":"Ma","year":"2011","journal-title":"Adv. Synth. Catal."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"42","DOI":"10.1016\/j.catcom.2017.09.019","article-title":"Fe(NO3)3\/2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ): An efficient catalyst system for selective oxidation of alcohols under aerobic conditions","volume":"103","author":"Hu","year":"2018","journal-title":"Catal. Commun."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/27\/12\/3727\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T23:27:18Z","timestamp":1760138838000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/27\/12\/3727"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,6,9]]},"references-count":46,"journal-issue":{"issue":"12","published-online":{"date-parts":[[2022,6]]}},"alternative-id":["molecules27123727"],"URL":"https:\/\/doi.org\/10.3390\/molecules27123727","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,6,9]]}}}