Literature DB >> 24420332

Zinc-catalyzed borylation of primary, secondary and tertiary alkyl halides with alkoxy diboron reagents at room temperature.

Shubhankar Kumar Bose1, Katharina Fucke, Lei Liu, Patrick G Steel, Todd B Marder.   

Abstract

A new catalytic system based on a Zn(II) NHC precursor has been developed for the cross-coupling reaction of alkyl halides with diboron reagents, which represents a novel use of a Group XII catalyst for CX borylation. This approach gives borylations of unactivated primary, secondary, and tertiary alkyl halides at room temperature to furnish alkyl boronates, with good functional-group compatibility, under mild conditions. Preliminary mechanistic investigations demonstrated that this borylation reaction seems to involve one-electron processes.
Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  N-heterocyclic carbenes; Suzuki-Miyaura; boronate esters; cross-coupling; homogeneous catalysis

Year:  2014        PMID: 24420332     DOI: 10.1002/anie.201308855

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  20 in total

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Journal:  Proc Natl Acad Sci U S A       Date:  2021-08-24       Impact factor: 11.205

5.  NHC induced radical formation via homolytic cleavage of B-B bonds and its role in organic reactions.

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6.  Visible Light-Induced Borylation of C-O, C-N, and C-X Bonds.

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7.  Boryl substitution of functionalized aryl-, heteroaryl- and alkenyl halides with silylborane and an alkoxy base: expanded scope and mechanistic studies.

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Journal:  Chem Sci       Date:  2015-03-02       Impact factor: 9.825

8.  Convenient and General Zinc-Catalyzed Borylation of Aryl Diazonium Salts and Aryltriazenes under Mild Conditions.

Authors:  Xinxin Qi; Li-Bing Jiang; Chao Zhou; Jin-Bao Peng; Xiao-Feng Wu
Journal:  ChemistryOpen       Date:  2017-03-16       Impact factor: 2.911

9.  Simple access to elusive α-boryl carbanions and their alkylation: an umpolung construction for organic synthesis.

Authors:  Kai Hong; Xun Liu; James P Morken
Journal:  J Am Chem Soc       Date:  2014-07-16       Impact factor: 15.419

10.  A Zinc Catalyzed C(sp3 )-C(sp2 ) Suzuki-Miyaura Cross-Coupling Reaction Mediated by Aryl-Zincates.

Authors:  Richard J Procter; Jay J Dunsford; Philip J Rushworth; David G Hulcoop; Richard A Layfield; Michael J Ingleson
Journal:  Chemistry       Date:  2017-10-19       Impact factor: 5.236

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