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Article: Transition-Metal-Free C(sp2)–C(sp2) Cross-Coupling of Diazo Quinones with Catechol Boronic Esters

TitleTransition-Metal-Free C(sp<sup>2</sup>)–C(sp<sup>2</sup>) Cross-Coupling of Diazo Quinones with Catechol Boronic Esters
Authors
Keywordsboronic esters
cross-coupling reactions
transition-metal-free reaction
C(sp2)−C(sp2) bond
diazo compounds
Issue Date2020
Citation
Angewandte Chemie - International Edition, 2020, v. 59, n. 37, p. 16202-16208 How to Cite?
Abstract© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim A transition-metal-free C(sp2)−C(sp2) bond formation reaction by the cross-coupling of diazo quinones with catechol boronic esters was developed. With this protocol, a variety of biaryls and alkenyl phenols were obtained in good to high yields under mild conditions. The reaction tolerates various functionalities and is applicable to the derivatization of pharmaceuticals and natural products. The synthetic utility of the method was demonstrated by the short synthesis of multi-substituted triphenylenes and three bioactive natural products, honokiol, moracin M, and stemofuran A. Mechanistic studies and density functional theory (DFT) calculations revealed that the reaction involves attack of the boronic ester by a singlet quinone carbene followed by a 1,2-rearrangement through a stepwise mechanism.
Persistent Identifierhttp://hdl.handle.net/10722/288821
ISSN
2019 Impact Factor: 12.959
2015 SCImago Journal Rankings: 6.229

 

DC FieldValueLanguage
dc.contributor.authorWu, Kai-
dc.contributor.authorWu, Liang Liang-
dc.contributor.authorZhou, Cong Ying-
dc.contributor.authorChe, Chi Ming-
dc.date.accessioned2020-10-12T08:05:57Z-
dc.date.available2020-10-12T08:05:57Z-
dc.date.issued2020-
dc.identifier.citationAngewandte Chemie - International Edition, 2020, v. 59, n. 37, p. 16202-16208-
dc.identifier.issn1433-7851-
dc.identifier.urihttp://hdl.handle.net/10722/288821-
dc.description.abstract© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim A transition-metal-free C(sp2)−C(sp2) bond formation reaction by the cross-coupling of diazo quinones with catechol boronic esters was developed. With this protocol, a variety of biaryls and alkenyl phenols were obtained in good to high yields under mild conditions. The reaction tolerates various functionalities and is applicable to the derivatization of pharmaceuticals and natural products. The synthetic utility of the method was demonstrated by the short synthesis of multi-substituted triphenylenes and three bioactive natural products, honokiol, moracin M, and stemofuran A. Mechanistic studies and density functional theory (DFT) calculations revealed that the reaction involves attack of the boronic ester by a singlet quinone carbene followed by a 1,2-rearrangement through a stepwise mechanism.-
dc.languageeng-
dc.relation.ispartofAngewandte Chemie - International Edition-
dc.subjectboronic esters-
dc.subjectcross-coupling reactions-
dc.subjecttransition-metal-free reaction-
dc.subjectC(sp2)−C(sp2) bond-
dc.subjectdiazo compounds-
dc.titleTransition-Metal-Free C(sp<sup>2</sup>)–C(sp<sup>2</sup>) Cross-Coupling of Diazo Quinones with Catechol Boronic Esters-
dc.typeArticle-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1002/anie.202006542-
dc.identifier.pmid32558142-
dc.identifier.scopuseid_2-s2.0-85087902168-
dc.identifier.volume59-
dc.identifier.issue37-
dc.identifier.spage16202-
dc.identifier.epage16208-
dc.identifier.eissn1521-3773-

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