{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,7]],"date-time":"2026-10-07T08:51:49Z","timestamp":1791363109141,"version":"4.3.1"},"reference-count":96,"publisher":"Wiley","issue":"49","license":[{"start":{"date-parts":[[2022,11,9]],"date-time":"2022-11-09T00:00:00Z","timestamp":1667952000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100018635","name":"Thousand Young Talents Program of China","doi-asserted-by":"publisher","award":["15-YINGXIA"],"award-info":[{"award-number":["15-YINGXIA"]}],"id":[{"id":"10.13039\/501100018635","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["22001180"],"award-info":[{"award-number":["22001180"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100018525","name":"Key Research and Development Program of Sichuan Province","doi-asserted-by":"publisher","award":["2021YFQ0060"],"award-info":[{"award-number":["2021YFQ0060"]}],"id":[{"id":"10.13039\/501100018525","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":[[2022,12,5]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The use of ketones as electrophiles to couple with arylboronic acid derivatives via C\u2212C bond activation has become a significant progress in the area of Suzuki\u2013Miyaura coupling (SMC) reaction, in which a permanent or temporary directing group is often required to promote the activation of the unstrained C\u2212C bond via oxidative addition. Herein, we disclosed the first example of directing group free formal SMC reaction of simple ketones with arylboronates via Rh\u2010catalyzed unstrained C\u2212C bond activation. A wide range of simple ketones, including aryl alkyl ketones, diaryl ketones and aryl perfluoroalkyl ketones, can serve as electrophiles to participate in the SMC reaction with aryl or perfluoroalkyl as the leaving group. The key to the success of this reaction is by means of nucleophilic addition\/\u03b2\u2010carbon elimination sequence that can activate the unstrained ketone carbonyl C\u2212C bond without the assistance of directing group.<\/jats:p>","DOI":"10.1002\/anie.202211080","type":"journal-article","created":{"date-parts":[[2022,10,10]],"date-time":"2022-10-10T15:23:02Z","timestamp":1665415382000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":20,"title":["Directing Group\u2010Free Formal Suzuki\u2013Miyaura Coupling of Simple Ketones Enabled by Activation of Unstrained C\u2212C Bonds"],"prefix":"10.1002","volume":"61","author":[{"given":"Jiangkun","family":"Huang","sequence":"first","affiliation":[{"name":"West China School of Public Health and West China Fourth Hospital and State Key Laboratory of Biotherapy Sichuan University  Chengdu 610041 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xufei","family":"Yan","sequence":"additional","affiliation":[{"name":"West China School of Public Health and West China Fourth Hospital and State Key Laboratory of Biotherapy Sichuan University  Chengdu 610041 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4803-8599","authenticated-orcid":false,"given":"Ying","family":"Xia","sequence":"additional","affiliation":[{"name":"West China School of Public Health and West China Fourth Hospital and State Key Laboratory of Biotherapy Sichuan University  Chengdu 610041 China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2022,11,9]]},"reference":[{"key":"e_1_2_3_1_1","unstructured":"\u00a0"},{"key":"e_1_2_3_2_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)95429-2"},{"key":"e_1_2_3_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00039a007"},{"key":"e_1_2_3_4_1","unstructured":"\u00a0"},{"key":"e_1_2_3_5_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201101379"},{"key":"e_1_2_3_5_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201101379"},{"key":"e_1_2_3_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.5b01409"},{"key":"e_1_2_3_7_1","unstructured":"For reviews see:"},{"key":"e_1_2_3_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar100082d"},{"key":"e_1_2_3_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr100259t"},{"key":"e_1_2_3_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.8b00410"},{"key":"e_1_2_3_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.0c00088"},{"key":"e_1_2_3_12_1","unstructured":"For reviews see:"},{"key":"e_1_2_3_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.5b00386"},{"key":"e_1_2_3_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.6b03277"},{"key":"e_1_2_3_15_2","doi-asserted-by":"publisher","DOI":"10.1039\/C8OB01832D"},{"key":"e_1_2_3_16_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201802635"},{"key":"e_1_2_3_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/asia.201801317"},{"key":"e_1_2_3_18_2","first-page":"649","volume":"20","author":"Li G.","year":"2020","journal-title":"Trends Chem."},{"key":"e_1_2_3_19_1","unstructured":"For other electrophiles used in SMC reactions see:"},{"key":"e_1_2_3_20_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200501582"},{"key":"e_1_2_3_20_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200501582"},{"key":"e_1_2_3_21_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201307019"},{"key":"e_1_2_3_21_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201307019"},{"key":"e_1_2_3_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.6b03434"},{"key":"e_1_2_3_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b10855"},{"key":"e_1_2_3_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b02312"},{"key":"e_1_2_3_25_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201908336"},{"key":"e_1_2_3_25_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201908336"},{"key":"e_1_2_3_26_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41586-019-0982-0"},{"key":"e_1_2_3_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.0c01462"},{"key":"e_1_2_3_28_1","unstructured":"For selective reviews 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unstrained ketone SMC reactions using permanent DG see:"},{"key":"e_1_2_3_43_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201206693"},{"key":"e_1_2_3_43_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201206693"},{"key":"e_1_2_3_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.6b01434"},{"key":"e_1_2_3_45_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b04068"},{"key":"e_1_2_3_46_2","doi-asserted-by":"publisher","DOI":"10.1039\/C8OB02075B"},{"key":"e_1_2_3_47_2","doi-asserted-by":"publisher","DOI":"10.1002\/ajoc.201900295"},{"key":"e_1_2_3_48_1","unstructured":"For unstrained ketone SMC reactions using temporary DG see:"},{"key":"e_1_2_3_49_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b02462"},{"key":"e_1_2_3_50_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.2c00110"},{"key":"e_1_2_3_51_1","unstructured":"For related examples using activated ketones see:"},{"key":"e_1_2_3_52_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol049833a"},{"key":"e_1_2_3_53_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol061359g"},{"key":"e_1_2_3_54_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.1c03048"},{"key":"e_1_2_3_55_1","unstructured":"For selected examples of non-ketone SMC reactions via C\u2212C activations see:"},{"key":"e_1_2_3_56_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja072577n"},{"key":"e_1_2_3_57_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol901217m"},{"key":"e_1_2_3_58_2","doi-asserted-by":"publisher","DOI":"10.1038\/ncomms8508"},{"key":"e_1_2_3_59_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201601914"},{"key":"e_1_2_3_59_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201601914"},{"key":"e_1_2_3_60_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41586-018-0628-7"},{"key":"e_1_2_3_61_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.9b05214"},{"key":"e_1_2_3_62_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202105355"},{"key":"e_1_2_3_62_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202105355"},{"key":"e_1_2_3_63_1","unstructured":"\u00a0"},{"key":"e_1_2_3_64_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja983197s"},{"key":"e_1_2_3_65_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0033537"},{"key":"e_1_2_3_66_1","unstructured":"For examples on \u03b2-aryl elimination see:"},{"key":"e_1_2_3_67_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja058550q"},{"key":"e_1_2_3_68_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200700902"},{"key":"e_1_2_3_68_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200700902"},{"key":"e_1_2_3_69_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo302592g"},{"key":"e_1_2_3_70_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.chempr.2019.04.008"},{"key":"e_1_2_3_71_1","unstructured":"For other related examples see:"},{"key":"e_1_2_3_72_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja980714y"},{"key":"e_1_2_3_73_2","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.82.778"},{"key":"e_1_2_3_74_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.2c02325"},{"key":"e_1_2_3_75_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chempr.2021.02.029"},{"key":"e_1_2_3_76_1","unstructured":"For examples on strained ketone SMC via \u03b2-C elimination see:"},{"key":"e_1_2_3_77_2","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.78.1528"},{"key":"e_1_2_3_78_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.6b01816"},{"key":"e_1_2_3_79_1","unstructured":"For selective examples on Rh-catalyzed reactions of ketones with arylboron reagents that give tertiary alcohols see:"},{"key":"e_1_2_3_80_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jorganchem.2006.02.022"},{"key":"e_1_2_3_81_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2009.10.082"},{"key":"e_1_2_3_82_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201104588"},{"key":"e_1_2_3_82_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201104588"},{"key":"e_1_2_3_83_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol300275s"},{"key":"e_1_2_3_84_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2sc01068b"},{"key":"e_1_2_3_85_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201600979"},{"key":"e_1_2_3_85_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201600979"}],"container-title":["Angewandte Chemie International 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