{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,22]],"date-time":"2026-03-22T03:55:37Z","timestamp":1774151737520,"version":"3.50.1"},"reference-count":92,"publisher":"Wiley","issue":"4","license":[{"start":{"date-parts":[[2021,10,14]],"date-time":"2021-10-14T00:00:00Z","timestamp":1634169600000},"content-version":"am","delay-in-days":321,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#am"},{"start":{"date-parts":[[2020,11,27]],"date-time":"2020-11-27T00:00:00Z","timestamp":1606435200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/100000165","name":"Division of Chemistry","doi-asserted-by":"publisher","award":["CHE-1664632"],"award-info":[{"award-number":["CHE-1664632"]}],"id":[{"id":"10.13039\/100000165","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":[[2021,1,25]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    A copper\u2010catalyzed carbonylative borylation of unactivated alkyl halides has been developed, enabling efficient synthesis of aliphatic potassium acyltrifluoroborates (KATs) in high yields by treating the in\u2005situ formed tetracoordinated acylboron intermediates with aqueous KHF\n                    <jats:sub>2<\/jats:sub>\n                    . A variety of functional groups are tolerated under the mild reaction conditions, and primary, secondary, and tertiary alkyl halides are all applicable. In addition, this method also provides facile access to\n                    <jats:italic>N<\/jats:italic>\n                    \u2010methyliminodiacetyl (MIDA) acylboronates as well as \u03b1\u2010methylated potassium acyltrifluoroborates in a one\u2010pot manner. Mechanistic studies indicate a radical atom transfer carbonylation (ATC) mechanism to form acyl halide intermediates that are subsequently borylated by (NHC)CuBpin.\n                  <\/jats:p>","DOI":"10.1002\/anie.202012373","type":"journal-article","created":{"date-parts":[[2020,10,14]],"date-time":"2020-10-14T14:31:09Z","timestamp":1602685869000},"page":"2094-2098","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":45,"title":["One\u2010Step Synthesis of Acylboron Compounds via Copper\u2010Catalyzed Carbonylative Borylation of Alkyl Halides**"],"prefix":"10.1002","volume":"60","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-3272-3276","authenticated-orcid":false,"given":"Li\u2010Jie","family":"Cheng","sequence":"first","affiliation":[{"name":"Department of Chemistry University of Illinois at Chicago  845 W. Taylor St. Chicago IL 60607 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Siling","family":"Zhao","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Illinois at Chicago  845 W. Taylor St. Chicago IL 60607 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6923-5164","authenticated-orcid":false,"given":"Neal P.","family":"Mankad","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Illinois at Chicago  845 W. Taylor St. Chicago IL 60607 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2020,11,27]]},"reference":[{"key":"e_1_2_2_1_1","doi-asserted-by":"publisher","DOI":"10.1002\/9783527639328"},{"key":"e_1_2_2_2_1","unstructured":"For reviews on acylboron compounds see:"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.5b00790"},{"key":"e_1_2_2_4_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5OB02118A"},{"key":"e_1_2_2_5_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6OB02425D"},{"key":"e_1_2_2_6_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202005050"},{"key":"e_1_2_2_6_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202005050"},{"key":"e_1_2_2_7_1","unstructured":"\u00a0"},{"key":"e_1_2_2_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00883a020"},{"key":"e_1_2_2_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00890a033"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar50015a001"},{"key":"e_1_2_2_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00987a042"},{"key":"e_1_2_2_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00987a043"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/om00024a069"},{"key":"e_1_2_2_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja073037t"},{"key":"e_1_2_2_15_1","unstructured":"\u00a0"},{"key":"e_1_2_2_16_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201201077"},{"key":"e_1_2_2_16_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201201077"},{"key":"e_1_2_2_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja5018442"},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b00059"},{"key":"e_1_2_2_19_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7SC00021A"},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0SC01330G"},{"key":"e_1_2_2_21_1","unstructured":"\u00a0"},{"key":"e_1_2_2_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo1004058"},{"key":"e_1_2_2_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol300668m"},{"key":"e_1_2_2_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.6b02652"},{"key":"e_1_2_2_25_1","unstructured":"\u00a0"},{"key":"e_1_2_2_26_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201403931"},{"key":"e_1_2_2_26_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201403931"},{"key":"e_1_2_2_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b00720"},{"key":"e_1_2_2_28_1","unstructured":"\u00a0"},{"key":"e_1_2_2_29_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201206501"},{"key":"e_1_2_2_29_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201206501"},{"key":"e_1_2_2_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.5b02741"},{"key":"e_1_2_2_31_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201611006"},{"key":"e_1_2_2_31_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201611006"},{"key":"e_1_2_2_32_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201707125"},{"key":"e_1_2_2_32_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201707125"},{"key":"e_1_2_2_33_1","unstructured":"\u00a0"},{"key":"e_1_2_2_34_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201707933"},{"key":"e_1_2_2_34_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201707933"},{"key":"e_1_2_2_35_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201901748"},{"key":"e_1_2_2_35_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201901748"},{"key":"e_1_2_2_36_1","doi-asserted-by":"publisher","DOI":"10.1039\/C9SC00378A"},{"key":"e_1_2_2_37_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201907349"},{"key":"e_1_2_2_37_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201907349"},{"key":"e_1_2_2_38_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201507627"},{"key":"e_1_2_2_38_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201507627"},{"key":"e_1_2_2_39_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201904576"},{"key":"e_1_2_2_39_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201904576"},{"key":"e_1_2_2_40_1","unstructured":"For recent examples of CO insertion with frustrated Lewis pairs to form acylborons see:"},{"key":"e_1_2_2_41_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201307551"},{"key":"e_1_2_2_41_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201307551"},{"key":"e_1_2_2_42_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja401492s"},{"key":"e_1_2_2_43_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201803823"},{"key":"e_1_2_2_44_1","unstructured":"\u00a0"},{"key":"e_1_2_2_45_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b05205"},{"key":"e_1_2_2_46_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b12582"},{"key":"e_1_2_2_47_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201804883"},{"key":"e_1_2_2_47_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201804883"},{"key":"e_1_2_2_48_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201801814"},{"key":"e_1_2_2_48_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201801814"},{"key":"e_1_2_2_49_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b12043"},{"key":"e_1_2_2_50_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b04092"},{"key":"e_1_2_2_51_1","unstructured":"For recent reviews see:"},{"key":"e_1_2_2_52_2","doi-asserted-by":"publisher","DOI":"10.1039\/c4cy00070f"},{"key":"e_1_2_2_53_2","doi-asserted-by":"publisher","DOI":"10.1002\/tcr.201000029"},{"key":"e_1_2_2_54_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.5b02973"},{"key":"e_1_2_2_55_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.6b00366"},{"key":"e_1_2_2_56_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0CS00316F"},{"key":"e_1_2_2_57_1","unstructured":"\u00a0"},{"key":"e_1_2_2_58_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja064019z"},{"key":"e_1_2_2_59_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol100468f"},{"key":"e_1_2_2_60_1","unstructured":"\u00a0"},{"key":"e_1_2_2_61_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201106299"},{"key":"e_1_2_2_61_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201106299"},{"key":"e_1_2_2_62_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol203413w"},{"key":"e_1_2_2_63_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.6b02918"},{"key":"e_1_2_2_64_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6OB02369J"},{"key":"e_1_2_2_65_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b01951"},{"key":"e_1_2_2_66_1","unstructured":"See Supporting Information for more details."},{"key":"e_1_2_2_67_1","unstructured":"\u00a0"},{"key":"e_1_2_2_68_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201500235"},{"key":"e_1_2_2_69_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5CC02316E"},{"key":"e_1_2_2_70_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201405829"},{"key":"e_1_2_2_71_1","unstructured":"Allylation and benzylation reactions were also promising but require further optimization."},{"key":"e_1_2_2_72_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201300443"},{"key":"e_1_2_2_73_1","unstructured":"Reviews on radical carbonylation:"},{"key":"e_1_2_2_74_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar600015v"},{"key":"e_1_2_2_75_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar500035q"},{"key":"e_1_2_2_76_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9CY00938H"},{"key":"e_1_2_2_77_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0QO00214C"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202012373","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.202012373","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/am-pdf\/10.1002\/anie.202012373","content-type":"application\/pdf","content-version":"am","intended-application":"syndication"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202012373","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,8,30]],"date-time":"2023-08-30T13:26:31Z","timestamp":1693401991000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202012373"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,11,27]]},"references-count":92,"journal-issue":{"issue":"4","published-print":{"date-parts":[[2021,1,25]]}},"alternative-id":["10.1002\/anie.202012373"],"URL":"https:\/\/doi.org\/10.1002\/anie.202012373","archive":["Portico"],"relation":{"has-preprint":[{"id-type":"doi","id":"10.26434\/chemrxiv.12818180.v1","asserted-by":"object"}]},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2020,11,27]]},"assertion":[{"value":"2020-09-10","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2020-11-27","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}