Literature DB >> 26257439

A modified procedure for the palladium catalyzed borylation/Suzuki-Miyaura cross-coupling of aryl and heteroaryl halides utilizing bis-boronic acid.

Gary A Molander1, Sarah L J Trice1, Brittany Tschaen1.   

Abstract

A modified Pd-catalyzed method of forming aryl- and heteroarylboron species and a two-step, one-pot borylation/Suzuki-Miyaura cross coupling using the atom economical tetrahydroxydiboron (bis-boronic acid, BBA) is reported. By using ethylene glycol as an additive, the new method results in increased yields, lower BBA loading, faster reaction times, and a broader reaction scope, including previously problematic substrates such as heterocycles.

Entities:  

Keywords:  Borylation; Cross-Coupling; Tetrahydroxydiboron; bis-Boronic Acid

Year:  2015        PMID： 26257439      PMCID： PMC4525720          DOI： 10.1016/j.tet.2015.04.026

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  15 in total

1.  Boron-masking strategy for the selective synthesis of oligoarenes via iterative Suzuki-Miyaura coupling.

Authors:  Hiroyoshi Noguchi; Kosho Hojo; Michinori Suginome
Journal:  J Am Chem Soc       Date:  2007-01-31       Impact factor: 15.419

2.  Scope of the two-step, one-pot palladium-catalyzed borylation/Suzuki cross-coupling reaction utilizing bis-boronic acid.

Authors:  Gary A Molander; Sarah L J Trice; Steven M Kennedy
Journal:  J Org Chem       Date:  2012-09-20       Impact factor: 4.354

3.  Palladium-catalyzed borylation of ortho-substituted phenyl halides and application to the one-pot synthesis of 2,2'-disubstituted biphenyls.

Authors:  O Baudoin; D Guénard; F Guéritte
Journal:  J Org Chem       Date:  2000-12-29       Impact factor: 4.354

4.  A new palladium precatalyst allows for the fast Suzuki-Miyaura coupling reactions of unstable polyfluorophenyl and 2-heteroaryl boronic acids.

Authors:  Tom Kinzel; Yong Zhang; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2010-10-13       Impact factor: 15.419

5.  Palladium-catalyzed, direct boronic acid synthesis from aryl chlorides: a simplified route to diverse boronate ester derivatives.

Authors:  Gary A Molander; Sarah L J Trice; Spencer D Dreher
Journal:  J Am Chem Soc       Date:  2010-11-24       Impact factor: 15.419

6.  Scope of the palladium-catalyzed aryl borylation utilizing bis-boronic acid.

Authors:  Gary A Molander; Sarah L J Trice; Steven M Kennedy; Spencer D Dreher; Matthew T Tudge
Journal:  J Am Chem Soc       Date:  2012-07-06       Impact factor: 15.419

7.  Nickel-catalyzed borylation of halides and pseudohalides with tetrahydroxydiboron [B2(OH)4].

Authors:  Gary A Molander; Livia N Cavalcanti; Carolina García-García
Journal:  J Org Chem       Date:  2013-06-18       Impact factor: 4.354

8.  A general solution for unstable boronic acids: slow-release cross-coupling from air-stable MIDA boronates.

Authors:  David M Knapp; Eric P Gillis; Martin D Burke
Journal:  J Am Chem Soc       Date:  2009-05-27       Impact factor: 15.419

9.  Organotrifluoroborates and monocoordinated palladium complexes as catalysts--a perfect combination for Suzuki-Miyaura coupling.

Authors:  Gary A Molander; Belgin Canturk
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

10.  Scope of the Suzuki-Miyaura cross-coupling reactions of potassium heteroaryltrifluoroborates.

Authors:  Gary A Molander; Belgin Canturk; Lauren E Kennedy
Journal:  J Org Chem       Date:  2009-02-06       Impact factor: 4.354
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  4 in total

1.  Zirconium-Redox-Shuttled Cross-Electrophile Coupling of Aromatic and Heteroaromatic Halides.

Authors:  Ting-Feng Wu; Yue-Jiao Zhang; Yue Fu; Fang-Jie Liu; Jian-Tao Tang; Peng Liu; F Dean Toste; Baihua Ye
Journal:  Chem       Date:  2021-07-08       Impact factor: 25.832

2.  Copper-catalyzed synthesis of allenylboronic acids. Access to sterically encumbered homopropargylic alcohols and amines by propargylboration.

Authors:  Jian Zhao; Sybrand J T Jonker; Denise N Meyer; Göran Schulz; C Duc Tran; Lars Eriksson; Kálmán J Szabó
Journal:  Chem Sci       Date:  2018-02-19       Impact factor: 9.825

3.  LiCl-Accelerated Multimetallic Cross-Coupling of Aryl Chlorides with Aryl Triflates.

Authors:  Liangbin Huang; Laura K G Ackerman; Kai Kang; Astrid M Parsons; Daniel J Weix
Journal:  J Am Chem Soc       Date:  2019-07-09       Impact factor: 15.419

4.  Protection-Free Strategy for the Synthesis of Boro-Depsipeptides in Aqueous Media under Microwave-Assisted Conditions.

Authors:  Shuo-Bei Qiu; Pei-Yao Liu; Bo-Cheng Wang; Pin-Rui Chen; Jing-Han Xiao; Ting-Yu Hsu; Kuan-Lin Pan; Zhi-Yin Lai; Yi-Wei Chen; Ying-Chuan Chen; Jen-Kun Chen; Po-Shen Pan
Journal:  Molecules       Date:  2022-04-04       Impact factor: 4.411
  4 in total

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