{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,27]],"date-time":"2026-09-27T15:18:25Z","timestamp":1790522305598,"version":"4.1.0"},"reference-count":121,"publisher":"Wiley","issue":"24","license":[{"start":{"date-parts":[[2021,5,6]],"date-time":"2021-05-06T00:00:00Z","timestamp":1620259200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100000196","name":"Canada Foundation for Innovation","doi-asserted-by":"publisher","award":["CFI-33858"],"award-info":[{"award-number":["CFI-33858"]}],"id":[{"id":"10.13039\/501100000196","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100004349","name":"BASF","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100004349","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["21702182"],"award-info":[{"award-number":["21702182"]}],"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":["21873081"],"award-info":[{"award-number":["21873081"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100012226","name":"Fundamental Research Funds for the Central Universities","doi-asserted-by":"publisher","award":["2020XZZX002-02"],"award-info":[{"award-number":["2020XZZX002-02"]}],"id":[{"id":"10.13039\/501100012226","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100011309","name":"State Key Laboratory of Clean Energy Utilization","doi-asserted-by":"publisher","award":["ZJUCEU2020007"],"award-info":[{"award-number":["ZJUCEU2020007"]}],"id":[{"id":"10.13039\/501100011309","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2021,6,7]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    The direct conversion of alkyl esters to ketones has been hindered by the sluggish reactivity of the starting materials and the susceptibility of the product towards subsequent nucleophilic attack. We have now achieved a cross\u2010coupling approach to this transformation using nickel, a bulky N\u2010heterocyclic carbene ligand, and alkyl organoboron coupling partners. 65 alkyl ketones bearing diverse functional groups and heterocyclic scaffolds have been synthesized with this method. Catalyst\u2010controlled chemoselectivity is observed for C(acyl)\u2212O bond activation of multi\u2010functional substrates bearing other bonds prone to cleavage by Ni, including aryl ether, aryl fluoride, and N\u2010Ph amide functional groups. Density functional theory calculations provide mechanistic support for a Ni\n                    <jats:sup>0<\/jats:sup>\n                    \/Ni\n                    <jats:sup>II<\/jats:sup>\n                    catalytic cycle and demonstrate how stabilizing non\u2010covalent interactions between the bulky catalyst and substrate are critical for the reaction's success.\n                  <\/jats:p>","DOI":"10.1002\/anie.202103327","type":"journal-article","created":{"date-parts":[[2021,4,1]],"date-time":"2021-04-01T04:16:47Z","timestamp":1617250607000},"page":"13476-13483","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":42,"title":["Direct Synthesis of Ketones from Methyl Esters by Nickel\u2010Catalyzed Suzuki\u2013Miyaura Coupling"],"prefix":"10.1002","volume":"60","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-2915-5319","authenticated-orcid":false,"given":"Yan\u2010Long","family":"Zheng","sequence":"first","affiliation":[{"name":"Centre for Catalysis Research and Innovation Department of Chemistry and Biomolecular Sciences University of Ottawa  10 Marie-Curie Ottawa Ontario K1N 6N5 Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Pei\u2010Pei","family":"Xie","sequence":"additional","affiliation":[{"name":"Department of Chemistry Zhejiang University  Hangzhou 310027 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Omid","family":"Daneshfar","sequence":"additional","affiliation":[{"name":"Centre for Catalysis Research and Innovation Department of Chemistry and Biomolecular Sciences University of Ottawa  10 Marie-Curie Ottawa Ontario K1N 6N5 Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8387-5261","authenticated-orcid":false,"given":"Kendall N.","family":"Houk","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry University of California  Los Angeles CA 90095 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xin","family":"Hong","sequence":"additional","affiliation":[{"name":"Department of Chemistry Zhejiang University  Hangzhou 310027 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1949-5069","authenticated-orcid":false,"given":"Stephen G.","family":"Newman","sequence":"additional","affiliation":[{"name":"Centre for Catalysis Research and Innovation Department of Chemistry and Biomolecular Sciences University of Ottawa  10 Marie-Curie Ottawa Ontario K1N 6N5 Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2021,5,6]]},"reference":[{"key":"e_1_2_6_1_1","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm200187y"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.6b00153"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201107017"},{"key":"e_1_2_6_4_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201107017"},{"key":"e_1_2_6_5_1","unstructured":"\u00a0"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00039a007"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.organomet.8b00720"},{"key":"e_1_2_6_8_1","unstructured":"\u00a0"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9CS00837C"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1007\/128_2013_494"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.7b01058"},{"key":"e_1_2_6_12_1","unstructured":"See reviews on Ni-catalyzed C\u2212O bond activation:"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.6b02964"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.5b00051"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar500345f"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4CS00206G"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr100259t"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.0c03334"},{"key":"e_1_2_6_19_1","unstructured":"See reviews on carboxylic acid derivative as cross-coupling electrophiles:"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.8b00023"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7CS00182G"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.8b00410"},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.6b03277"},{"key":"e_1_2_6_24_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201704670"},{"key":"e_1_2_6_25_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(99)00184-2"},{"key":"e_1_2_6_26_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)91316-4"},{"key":"e_1_2_6_27_1","unstructured":"\u00a0"},{"key":"e_1_2_6_28_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1977.1423"},{"key":"e_1_2_6_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00479a077"},{"key":"e_1_2_6_30_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(98)00456-0"},{"key":"e_1_2_6_31_1","unstructured":"\u00a0"},{"key":"e_1_2_6_32_2","doi-asserted-by":"publisher","DOI":"10.3390\/catal9010053"},{"key":"e_1_2_6_33_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja005613q"},{"key":"e_1_2_6_34_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol034962x"},{"key":"e_1_2_6_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo049964p"},{"key":"e_1_2_6_36_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20010917)40:18<3458::AID-ANIE3458>3.0.CO;2-0"},{"key":"e_1_2_6_36_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20010917)113:18<3566::AID-ANGE3566>3.0.CO;2-0"},{"key":"e_1_2_6_37_2","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.75.137"},{"key":"e_1_2_6_38_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4RA11520A"},{"key":"e_1_2_6_39_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201906000"},{"key":"e_1_2_6_39_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201906000"},{"key":"e_1_2_6_40_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202002271"},{"key":"e_1_2_6_40_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202002271"},{"key":"e_1_2_6_41_1","unstructured":"\u00a0"},{"key":"e_1_2_6_42_2","doi-asserted-by":"publisher","DOI":"10.1038\/nature14615"},{"key":"e_1_2_6_43_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.2388"},{"key":"e_1_2_6_44_2","doi-asserted-by":"publisher","DOI":"10.1038\/ncomms11554"},{"key":"e_1_2_6_45_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201607856"},{"key":"e_1_2_6_45_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201607856"},{"key":"e_1_2_6_46_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201601914"},{"key":"e_1_2_6_46_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201601914"},{"key":"e_1_2_6_47_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201707102"},{"key":"e_1_2_6_47_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201707102"},{"key":"e_1_2_6_48_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.6b02323"},{"key":"e_1_2_6_49_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.6b03616"},{"key":"e_1_2_6_50_1","unstructured":"\u00a0"},{"key":"e_1_2_6_51_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00531a016"},{"key":"e_1_2_6_52_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20020402)41:7<1237::AID-ANIE1237>3.0.CO;2-F"},{"key":"e_1_2_6_52_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20020402)114:7<1285::AID-ANGE1285>3.0.CO;2-Y"},{"key":"e_1_2_6_53_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol048513o"},{"key":"e_1_2_6_54_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja306062c"},{"key":"e_1_2_6_55_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201304492"},{"key":"e_1_2_6_55_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201304492"},{"key":"e_1_2_6_56_2","doi-asserted-by":"publisher","DOI":"10.1038\/ncomms8508"},{"key":"e_1_2_6_57_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b00049"},{"key":"e_1_2_6_58_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201604696"},{"key":"e_1_2_6_58_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201604696"},{"key":"e_1_2_6_59_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201612624"},{"key":"e_1_2_6_59_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201612624"},{"key":"e_1_2_6_60_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201611819"},{"key":"e_1_2_6_60_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201611819"},{"key":"e_1_2_6_61_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b12329"},{"key":"e_1_2_6_62_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.7b00245"},{"key":"e_1_2_6_63_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7SC02692G"},{"key":"e_1_2_6_64_1","unstructured":"\u00a0"},{"key":"e_1_2_6_65_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.6b00793"},{"key":"e_1_2_6_66_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b01021"},{"key":"e_1_2_6_67_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b02911"},{"key":"e_1_2_6_68_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.1268"},{"key":"e_1_2_6_69_2","doi-asserted-by":"publisher","DOI":"10.1002\/ajoc.201200066"},{"key":"e_1_2_6_70_1","unstructured":"\u00a0"},{"key":"e_1_2_6_71_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b12865"},{"key":"e_1_2_6_72_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b01646"},{"key":"e_1_2_6_73_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.6b00801"},{"key":"e_1_2_6_74_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201511486"},{"key":"e_1_2_6_74_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201511486"},{"key":"e_1_2_6_75_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b03669"},{"key":"e_1_2_6_76_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b01233"},{"key":"e_1_2_6_77_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201808560"},{"key":"e_1_2_6_77_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201808560"},{"key":"e_1_2_6_78_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201911372"},{"key":"e_1_2_6_78_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201911372"},{"key":"e_1_2_6_79_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b06191"},{"key":"e_1_2_6_80_1","unstructured":"\u00a0"},{"key":"e_1_2_6_81_2","doi-asserted-by":"publisher","DOI":"10.1039\/C3CS60197H"},{"key":"e_1_2_6_82_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja011306o"},{"key":"e_1_2_6_83_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja074008l"},{"key":"e_1_2_6_84_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja301612y"},{"key":"e_1_2_6_85_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejic.201402830"},{"key":"e_1_2_6_86_1","unstructured":"\u00a0"},{"key":"e_1_2_6_87_2","doi-asserted-by":"publisher","DOI":"10.1021\/om200349y"},{"key":"e_1_2_6_88_2","doi-asserted-by":"publisher","DOI":"10.1021\/cs400429j"},{"key":"e_1_2_6_89_1","unstructured":"For examples where remote steric bulk improves reactivity in Ni catalysis:"},{"key":"e_1_2_6_90_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-019-0409-4"},{"key":"e_1_2_6_91_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.2741"},{"key":"e_1_2_6_92_1","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.20160391"},{"key":"e_1_2_6_93_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41586-018-0628-7"},{"key":"e_1_2_6_94_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202000124"},{"key":"e_1_2_6_94_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202000124"},{"key":"e_1_2_6_95_1","unstructured":"\u00a0"},{"key":"e_1_2_6_96_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200801447"},{"key":"e_1_2_6_96_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200801447"},{"key":"e_1_2_6_97_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja207759e"},{"key":"e_1_2_6_98_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.9b00884"},{"key":"e_1_2_6_99_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules23102681"},{"key":"e_1_2_6_100_1","unstructured":"For related mechanistic studies involving organoboron-K3PO4complexes see:"},{"key":"e_1_2_6_101_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.9b02636"},{"key":"e_1_2_6_102_2","doi-asserted-by":"publisher","DOI":"10.1002\/asia.201700313"},{"key":"e_1_2_6_103_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.6b02093"},{"key":"e_1_2_6_104_1","unstructured":"The full free energy profile towards forming13is provided in the Supporting Information."}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202103327","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.202103327","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202103327","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,8,21]],"date-time":"2023-08-21T18:30:22Z","timestamp":1692642622000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202103327"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,5,6]]},"references-count":121,"journal-issue":{"issue":"24","published-print":{"date-parts":[[2021,6,7]]}},"alternative-id":["10.1002\/anie.202103327"],"URL":"https:\/\/doi.org\/10.1002\/anie.202103327","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,5,6]]},"assertion":[{"value":"2021-03-07","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2021-05-06","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}