Literature DB >> 27267542

Palladium-Catalyzed ipso-Borylation of Aryl Sulfides with Diborons.

M Bhanuchandra1, Alexandre Baralle1, Shinya Otsuka1, Keisuke Nogi1, Hideki Yorimitsu1, Atsuhiro Osuka1.   

Abstract

A catalytic Miyaura-type ipso-borylation of aryl sulfides with diboron reagents has been achieved, providing arylboronate esters of synthetic use. The key conditions to transform inherently reluctant C-S bonds into C-B bonds include a palladium-NHC (N-heterocyclic carbene) precatalyst, bis(pinacolato)diboron, and lithium hexamethyldisilazide. This protocol is applicable to a reasonable range of aryl alkyl sulfides. Twofold borylation was observed in the reaction of diphenyl sulfide.

Entities:  

Year:  2016        PMID: 27267542     DOI: 10.1021/acs.orglett.6b01305

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  3 in total

1.  Enantioselective Synthesis of Biaryl Atropisomers via the Addition of Thiophenols into Aryl-Naphthoquinones.

Authors:  Sean M Maddox; Gregory A Dawson; Nicholas C Rochester; Arianna B Ayonon; Curtis E Moore; Arnold L Rheingold; Jeffrey L Gustafson
Journal:  ACS Catal       Date:  2018-05-08       Impact factor: 13.084

2.  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

3.  Rhodium-Catalyzed Decarbonylative Borylation of Aromatic Thioesters for Facile Diversification of Aromatic Carboxylic Acids.

Authors:  Hidenori Ochiai; Yuta Uetake; Takashi Niwa; Takamitsu Hosoya
Journal:  Angew Chem Int Ed Engl       Date:  2017-01-26       Impact factor: 15.336

  3 in total

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