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- PMID: 32558142
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Article: Transition‐Metal‐Free C(sp2)–C(sp2) Cross‐Coupling of Diazo Quinones with Catechol Boronic Esters
Title | Transition‐Metal‐Free C(sp2)–C(sp2) Cross‐Coupling of Diazo Quinones with Catechol Boronic Esters |
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Authors | |
Keywords | boronic esters cross-coupling reactions transition-metal-free reaction C(sp2)−C(sp2) bond diazo compounds |
Issue Date | 2020 |
Publisher | Wiley - VCH Verlag GmbH & Co. KGaA. The Journal's web site is located at https://onlinelibrary.wiley.com/journal/15213773 |
Citation | Angewandte Chemie (International Edition), 2020, v. 59 n. 37, p. 16202-16208 How to Cite? |
Abstract | 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. © 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim |
Persistent Identifier | http://hdl.handle.net/10722/288821 |
ISSN | 2021 Impact Factor: 16.823 2020 SCImago Journal Rankings: 5.831 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Wu, K | - |
dc.contributor.author | Wu, L | - |
dc.contributor.author | Zhou, C | - |
dc.contributor.author | Che, CM | - |
dc.date.accessioned | 2020-10-12T08:05:57Z | - |
dc.date.available | 2020-10-12T08:05:57Z | - |
dc.date.issued | 2020 | - |
dc.identifier.citation | Angewandte Chemie (International Edition), 2020, v. 59 n. 37, p. 16202-16208 | - |
dc.identifier.issn | 1433-7851 | - |
dc.identifier.uri | http://hdl.handle.net/10722/288821 | - |
dc.description.abstract | 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. © 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim | - |
dc.language | eng | - |
dc.publisher | Wiley - VCH Verlag GmbH & Co. KGaA. The Journal's web site is located at https://onlinelibrary.wiley.com/journal/15213773 | - |
dc.relation.ispartof | Angewandte Chemie (International Edition) | - |
dc.rights | This is the peer reviewed version of the following article: Angewandte Chemie (International Edition), 2020, v. 59 n. 37, p. 16202-16208, which has been published in final form at http://dx.doi.org/10.1002/anie.202006542. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. | - |
dc.subject | boronic esters | - |
dc.subject | cross-coupling reactions | - |
dc.subject | transition-metal-free reaction | - |
dc.subject | C(sp2)−C(sp2) bond | - |
dc.subject | diazo compounds | - |
dc.title | Transition‐Metal‐Free C(sp2)–C(sp2) Cross‐Coupling of Diazo Quinones with Catechol Boronic Esters | - |
dc.type | Article | - |
dc.identifier.email | Zhou, C: cyzhou@hku.hk | - |
dc.identifier.email | Che, CM: chemhead@hku.hk | - |
dc.identifier.authority | Wu, L=rp02732 | - |
dc.identifier.authority | Zhou, C=rp00843 | - |
dc.identifier.authority | Che, CM=rp00670 | - |
dc.description.nature | postprint | - |
dc.identifier.doi | 10.1002/anie.202006542 | - |
dc.identifier.pmid | 32558142 | - |
dc.identifier.scopus | eid_2-s2.0-85087902168 | - |
dc.identifier.hkuros | 324861 | - |
dc.identifier.volume | 59 | - |
dc.identifier.issue | 37 | - |
dc.identifier.spage | 16202 | - |
dc.identifier.epage | 16208 | - |
dc.identifier.eissn | 1521-3773 | - |
dc.identifier.isi | WOS:000548234300001 | - |
dc.publisher.place | Germany | - |
dc.identifier.issnl | 1433-7851 | - |