{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,24]],"date-time":"2026-09-24T19:16:44Z","timestamp":1790277404707,"version":"4.1.0"},"reference-count":473,"publisher":"Wiley","issue":"48","license":[{"start":{"date-parts":[[2020,8,26]],"date-time":"2020-08-26T00:00:00Z","timestamp":1598400000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/100000002","name":"National Institutes of Health","doi-asserted-by":"publisher","award":["GM-130395"],"award-info":[{"award-number":["GM-130395"]}],"id":[{"id":"10.13039\/100000002","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":[[2020,11,23]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>A copper\u2010based complex that contains a sulfonate N\u2010heterocyclic carbene ligand was first reported 15 years ago. Since then, these organometallic entities have proven to be uniquely effective in catalyzing an assortment of enantioselective transformations, including allylic substitutions, conjugate additions, proto\u2010boryl additions to alkenes, boryl and silyl substitutions, hydride\u2010allyl additions to alkenyl boronates, and additions of boron\u2010containing allyl moieties to N\u2010H ketimines. In this review article, we detail the shortcomings in the state\u2010of\u2010the\u2010art that fueled the development of this air stable ligand class, members of which can be prepared on multigram scale. For each reaction type, when relevant, the prior art at the time of the advance involving sulfonate NHC\u2010Cu catalysts and\/or subsequent key developments are briefly analyzed, and the relevance of the advance to efficient and enantioselective total or formal synthesis of biologically active molecules is underscored. Mechanistic analysis of the structural attributes of sulfonate NHC\u2010Cu catalysts that are responsible for their ability to facilitate transformations with high efficiency as well as regio\u2010 and enantioselectivity are detailed. This review contains several formerly undisclosed methodological advances and mechanistic analyses, the latter of which constitute a revision of previously reported proposals.<\/jats:p>","DOI":"10.1002\/anie.202003755","type":"journal-article","created":{"date-parts":[[2020,5,4]],"date-time":"2020-05-04T14:56:00Z","timestamp":1588604160000},"page":"21304-21359","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":71,"title":["Sulfonate N\u2010Heterocyclic Carbene\u2013Copper Complexes: Uniquely Effective Catalysts for Enantioselective Synthesis of C\u2212C, C\u2212B, C\u2212H, and C\u2212Si Bonds"],"prefix":"10.1002","volume":"59","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-1470-6456","authenticated-orcid":false,"given":"Amir H.","family":"Hoveyda","sequence":"first","affiliation":[{"name":"Department of Chemistry Merkert Chemistry Center Boston College  Chestnut Hill MA 02467 USA"},{"name":"Supramolecular Science and Engineering Institute University of Strasbourg CNRS  67000 Strasbourg France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yuebiao","family":"Zhou","sequence":"additional","affiliation":[{"name":"Department of Chemistry Merkert Chemistry Center Boston College  Chestnut Hill MA 02467 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ying","family":"Shi","sequence":"additional","affiliation":[{"name":"Department of Chemistry Merkert Chemistry Center Boston College  Chestnut Hill MA 02467 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"M. Kevin","family":"Brown","sequence":"additional","affiliation":[{"name":"Department of Chemistry Merkert Chemistry Center Boston College  Chestnut Hill MA 02467 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hao","family":"Wu","sequence":"additional","affiliation":[{"name":"Department of Chemistry Merkert Chemistry Center Boston College  Chestnut Hill MA 02467 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sebastian","family":"Torker","sequence":"additional","affiliation":[{"name":"Department of Chemistry Merkert Chemistry Center Boston College  Chestnut Hill MA 02467 USA"},{"name":"Supramolecular Science and Engineering Institute University of Strasbourg CNRS  67000 Strasbourg France"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2020,8,26]]},"reference":[{"key":"e_1_2_13_1_1","unstructured":"\u00a0"},{"key":"e_1_2_13_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja020259c"},{"key":"e_1_2_13_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0302228"},{"key":"e_1_2_13_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0458672"},{"key":"e_1_2_13_5_1","unstructured":"\u00a0"},{"key":"e_1_2_13_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja046245j"},{"key":"e_1_2_13_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja050179j"},{"key":"e_1_2_13_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja067456m"},{"key":"e_1_2_13_9_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200700841"},{"key":"e_1_2_13_9_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200700841"},{"key":"e_1_2_13_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja062061o"},{"key":"e_1_2_13_11_1","unstructured":"\u00a0"},{"key":"e_1_2_13_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja046310p"},{"key":"e_1_2_13_13_2","doi-asserted-by":"publisher","DOI":"10.1039\/b907036b"},{"key":"e_1_2_13_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar200191k"},{"key":"e_1_2_13_15_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200604511"},{"key":"e_1_2_13_15_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200604511"},{"key":"e_1_2_13_16_1","unstructured":"For reviews on catalytic EAS reactions with \u201chard\u201d alkyl- or arylmetal-based reagents see:"},{"key":"e_1_2_13_17_2","doi-asserted-by":"publisher","DOI":"10.1039\/b401123f"},{"key":"e_1_2_13_18_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200500653"},{"key":"e_1_2_13_18_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200500653"},{"key":"e_1_2_13_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr0683515"},{"key":"e_1_2_13_20_2","first-page":"497","volume-title":"Catalytic Asymmetric Synthesis","author":"Helmchen G.","year":"2010"},{"key":"e_1_2_13_21_2","doi-asserted-by":"publisher","DOI":"10.1002\/9783527664573.ch4"},{"key":"e_1_2_13_22_2","doi-asserted-by":"publisher","DOI":"10.1002\/9783527664573.ch14"},{"key":"e_1_2_13_23_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200700501"},{"key":"e_1_2_13_23_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200700501"},{"key":"e_1_2_13_24_1","unstructured":"For examples of EAS reactions involving dialkyl- and diarylzinc reagents where sulfonate-containing NHC-Cu complexes were used to generate allylsilane products see: ref.\u2005[2d]."},{"key":"e_1_2_13_25_1","doi-asserted-by":"crossref","first-page":"733","DOI":"10.1016\/B978-0-08-052349-1.00244-4","volume-title":"Comprehensive Organic Synthesis, Vol.\u20058","author":"Eisch J. 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Chem."},{"key":"e_1_2_13_45_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol049346v"},{"key":"e_1_2_13_46_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201303501"},{"key":"e_1_2_13_46_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201303501"},{"key":"e_1_2_13_47_1","unstructured":"For reviews regarding the utility of allenes in chemical synthesis See:"},{"key":"e_1_2_13_48_2","doi-asserted-by":"publisher","DOI":"10.1002\/9783527619573"},{"key":"e_1_2_13_49_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-2007-965963"},{"key":"e_1_2_13_50_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201002366"},{"key":"e_1_2_13_51_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201101460"},{"key":"e_1_2_13_51_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201101460"},{"key":"e_1_2_13_52_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja2010829"},{"key":"e_1_2_13_53_1","unstructured":"For subsequent reports regarding EAS of an aryl moiety catalyzed by a Cu-based complex see:"},{"key":"e_1_2_13_54_2","doi-asserted-by":"publisher","DOI":"10.1039\/b809140d"},{"key":"e_1_2_13_55_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200801309"},{"key":"e_1_2_13_56_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200904676"},{"key":"e_1_2_13_56_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200904676"},{"key":"e_1_2_13_57_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200801879"},{"key":"e_1_2_13_58_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo102386s"},{"key":"e_1_2_13_59_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201103581"},{"key":"e_1_2_13_59_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201103581"},{"key":"e_1_2_13_60_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.5b03396"},{"key":"e_1_2_13_61_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b02992"},{"key":"e_1_2_13_62_1","unstructured":"For related processes to generate a tertiary carbon stereogenic center catalyzed by Pd-based complexes see:"},{"key":"e_1_2_13_63_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja054109o"},{"key":"e_1_2_13_64_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol7018532"},{"key":"e_1_2_13_65_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol200602x"},{"key":"e_1_2_13_66_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol102977b"},{"key":"e_1_2_13_67_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol300770w"},{"key":"e_1_2_13_68_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4OB02574A"},{"key":"e_1_2_13_69_1","unstructured":"For reports of EAS of an aryl moiety to generate a tertiary carbon stereogenic center catalyzed by a Ir-based complex see:"},{"key":"e_1_2_13_70_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol800409d"},{"key":"e_1_2_13_71_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b02678"},{"key":"e_1_2_13_72_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b01346"},{"key":"e_1_2_13_73_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b01631"},{"key":"e_1_2_13_74_1","unstructured":"For related processes that afford a tertiary stereogenic carbon center and are catalyzed by Rh-based complexes see:"},{"key":"e_1_2_13_75_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200600275"},{"key":"e_1_2_13_76_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol061777l"},{"key":"e_1_2_13_77_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol3019902"},{"key":"e_1_2_13_78_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.2360"},{"key":"e_1_2_13_79_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja980499l"},{"key":"e_1_2_13_80_2","doi-asserted-by":"publisher","DOI":"10.1039\/b002547j"},{"key":"e_1_2_13_81_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol100841y"},{"key":"e_1_2_13_82_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol101171v"},{"key":"e_1_2_13_83_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201005124"},{"key":"e_1_2_13_83_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201005124"},{"key":"e_1_2_13_84_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.aaw4029"},{"key":"e_1_2_13_85_1","unstructured":"For selected reviews see:"},{"key":"e_1_2_13_86_2","unstructured":"ref.\u2009[24]. 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For a related transformation see:"},{"key":"e_1_2_13_137_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201703380"},{"key":"e_1_2_13_137_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201703380"},{"key":"e_1_2_13_138_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b05805"},{"key":"e_1_2_13_139_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja3093955"},{"key":"e_1_2_13_140_1","doi-asserted-by":"publisher","DOI":"10.1021\/om00061a005"},{"key":"e_1_2_13_141_1","unstructured":"\u00a0"},{"key":"e_1_2_13_142_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja105176v"},{"key":"e_1_2_13_143_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol201115k"},{"key":"e_1_2_13_144_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo3004293"},{"key":"e_1_2_13_145_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo3015165"},{"key":"e_1_2_13_146_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol503111h"},{"key":"e_1_2_13_147_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0034-1378561"},{"key":"e_1_2_13_148_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja500029w"},{"key":"e_1_2_13_149_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja510266x"},{"key":"e_1_2_13_150_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b03477"},{"key":"e_1_2_13_151_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201507171"},{"key":"e_1_2_13_151_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201507171"},{"key":"e_1_2_13_152_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201509840"},{"key":"e_1_2_13_152_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201509840"},{"key":"e_1_2_13_153_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.6b00719"},{"key":"e_1_2_13_154_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201603465"},{"key":"e_1_2_13_154_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201603465"},{"key":"e_1_2_13_155_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201705829"},{"key":"e_1_2_13_155_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201705829"},{"key":"e_1_2_13_156_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b09309"},{"key":"e_1_2_13_157_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7OB02978K"},{"key":"e_1_2_13_158_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201600309"},{"key":"e_1_2_13_158_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201600309"},{"key":"e_1_2_13_159_1","unstructured":"\u00a0"},{"key":"e_1_2_13_160_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja5071202"},{"key":"e_1_2_13_161_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b05477"},{"key":"e_1_2_13_162_1","unstructured":"K.\u2005P. McGrath A.\u2005H. Hoveyda previously unpublished results. See the Supporting Information for details."},{"key":"e_1_2_13_163_1","unstructured":"Y. Zhou Z. Huang Y. Shi A.\u2005H. Hoveyda previously unpublished results. See the Supporting Information for details."},{"key":"e_1_2_13_164_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b04902"},{"key":"e_1_2_13_165_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b11382"},{"key":"e_1_2_13_166_1","unstructured":"\u00a0"},{"key":"e_1_2_13_167_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201301018"},{"key":"e_1_2_13_167_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201301018"},{"key":"e_1_2_13_168_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja4007645"},{"key":"e_1_2_13_169_1","unstructured":"For example see:"},{"key":"e_1_2_13_170_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja4092819"},{"key":"e_1_2_13_171_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201304365"},{"key":"e_1_2_13_171_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201304365"},{"key":"e_1_2_13_172_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.2131"},{"key":"e_1_2_13_173_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201409104"},{"key":"e_1_2_13_173_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201409104"},{"key":"e_1_2_13_174_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201507594"},{"key":"e_1_2_13_174_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201507594"},{"key":"e_1_2_13_175_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b04816"},{"key":"e_1_2_13_176_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b11229"},{"key":"e_1_2_13_177_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201611444"},{"key":"e_1_2_13_177_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201611444"},{"key":"e_1_2_13_178_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201707070"},{"key":"e_1_2_13_178_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201707070"},{"key":"e_1_2_13_179_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201910707"},{"key":"e_1_2_13_179_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201910707"},{"key":"e_1_2_13_180_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8SC04505D"},{"key":"e_1_2_13_181_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b05465"},{"key":"e_1_2_13_182_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja904654j"},{"key":"e_1_2_13_183_1","unstructured":"Previously proposed mechanistic models involve two distinct scenarios: 1)\u2005Leaving group association with Cu (mainly in cases where soft N S and P donors are present); see:"},{"key":"e_1_2_13_184_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr078352c"},{"key":"e_1_2_13_185_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja302520h"},{"key":"e_1_2_13_186_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja804682r"},{"key":"e_1_2_13_187_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(00)00135-6"},{"key":"e_1_2_13_188_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200900054"},{"key":"e_1_2_13_189_1","unstructured":"\u00a0"},{"key":"e_1_2_13_190_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr50004a004"},{"key":"e_1_2_13_191_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr60211a004"},{"key":"e_1_2_13_192_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201107334"},{"key":"e_1_2_13_192_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201107334"},{"key":"e_1_2_13_193_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201503476"},{"key":"e_1_2_13_193_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201503476"},{"key":"e_1_2_13_194_1","unstructured":"For a stereochemical model regarding the related reaction involving a Na+-carboxylic ester interaction (cf. Scheme\u200522\u2009a) see the Supporting Information."},{"key":"e_1_2_13_195_1","unstructured":"For stereochemical models in connection with EAS involving alkynyl-Al compounds (Scheme\u20058) see the Supporting Information."},{"key":"e_1_2_13_196_1","unstructured":"For recent reviews on catalytic ECA with \u201chard\u201d alkyl- or arylmetal-based reagents see:"},{"key":"e_1_2_13_197_2","doi-asserted-by":"publisher","DOI":"10.1002\/9783527664573.ch2"},{"key":"e_1_2_13_198_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar0501976"},{"key":"e_1_2_13_199_2","unstructured":"Ref.\u2005[6c];"},{"key":"e_1_2_13_200_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr068424k"},{"key":"e_1_2_13_201_2","doi-asserted-by":"publisher","DOI":"10.1039\/b816853a"},{"key":"e_1_2_13_202_2","doi-asserted-by":"publisher","DOI":"10.1039\/c0cc02309d"},{"key":"e_1_2_13_203_2","doi-asserted-by":"publisher","DOI":"10.1002\/asia.200900512"},{"key":"e_1_2_13_204_1","unstructured":"\u00a0"},{"key":"e_1_2_13_205_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200462137"},{"key":"e_1_2_13_205_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200462137"},{"key":"e_1_2_13_206_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.1196"},{"key":"e_1_2_13_207_1","unstructured":"\u00a0"},{"key":"e_1_2_13_208_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja050800f"},{"key":"e_1_2_13_209_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201406247"},{"key":"e_1_2_13_209_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201406247"},{"key":"e_1_2_13_210_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja0553811"},{"key":"e_1_2_13_211_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja056692e"},{"key":"e_1_2_13_212_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja0629920"},{"key":"e_1_2_13_213_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200701290"},{"key":"e_1_2_13_214_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja003698p"},{"key":"e_1_2_13_215_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200802910"},{"key":"e_1_2_13_215_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200802910"},{"key":"e_1_2_13_216_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja8058414"},{"key":"e_1_2_13_217_1","unstructured":"\u00a0"},{"key":"e_1_2_13_218_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41586-019-1179-2"},{"key":"e_1_2_13_219_2","author":"peng C.","year":"2020","journal-title":"Angew. 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stereochemical models regarding Cu-B addition to F3C-substituted alkenes see ref.\u2009[51]."},{"key":"e_1_2_13_388_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00089a011"},{"key":"e_1_2_13_389_1","unstructured":"\u00a0"},{"key":"e_1_2_13_390_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201300648"},{"key":"e_1_2_13_390_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201300648"},{"key":"e_1_2_13_391_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0034-1378542"},{"key":"e_1_2_13_392_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201501371"},{"key":"e_1_2_13_393_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo400888b"},{"key":"e_1_2_13_394_1","unstructured":"H. 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