Literature DB >> 22894743

A general method for Suzuki-Miyaura coupling reactions using lithium triisopropyl borates.

Matthias A Oberli1, Stephen L Buchwald.   

Abstract

Conditions for the Suzuki-Miyaura coupling of lithium triisopropyl borates are reported, as well as a procedure for a one-pot lithiation, borylation, and subsequent Suzuki-Miyaura coupling of various heterocycles with aryl halides. These borate species are much more stable toward protodeboronation than the corresponding boronic acids and can conveniently be stored on benchtop at room temperature.

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Year:  2012        PMID： 22894743      PMCID： PMC3684691          DOI： 10.1021/ol302063g

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


  17 in total

1.  A highly active catalyst for Suzuki-Miyaura cross-coupling reactions of heteroaryl compounds.

Authors:  Kelvin L Billingsley; Kevin W Anderson; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2006-05-19       Impact factor: 15.336

2.  Organotrifluoroborates: protected boronic acids that expand the versatility of the Suzuki coupling reaction.

Authors:  Gary A Molander; Noel Ellis
Journal:  Acc Chem Res       Date:  2007-01-26       Impact factor: 22.384

3.  A simple and modular strategy for small molecule synthesis: iterative Suzuki-Miyaura coupling of B-protected haloboronic acid building blocks.

Authors:  Eric P Gillis; Martin D Burke
Journal:  J Am Chem Soc       Date:  2007-05-09       Impact factor: 15.419

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 Suzuki-Miyaura coupling of pyridyl-2-boronic esters with aryl halides using highly active and air-stable phosphine chloride and oxide ligands.

Authors:  David X Yang; Steven L Colletti; Kevin Wu; Maoying Song; George Y Li; Hong C Shen
Journal:  Org Lett       Date:  2009-01-15       Impact factor: 6.005

6.  Efficient Suzuki-Miyaura coupling of (hetero)aryl chlorides with thiophene- and furanboronic acids in aqueous n-butanol.

Authors:  Christoph A Fleckenstein; Herbert Plenio
Journal:  J Org Chem       Date:  2008-03-21       Impact factor: 4.354

7.  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

8.  An efficient synthesis and substitution of 3-aroyl-2-bromobenzo[b]furans.

Authors:  Gurmit S Gill; Damian W Grobelny; Jason H Chaplin; Bernard L Flynn
Journal:  J Org Chem       Date:  2008-01-05       Impact factor: 4.354

9.  Differentially protected benzenediboronic acids: divalent cross-coupling modules for the efficient synthesis of boron-substituted oligoarenes.

Authors:  Hiroyoshi Noguchi; Takayuki Shioda; Chih-Ming Chou; Michinori Suginome
Journal:  Org Lett       Date:  2008-01-10       Impact factor: 6.005

10.  Cyclic triolborates: air- and water-stable ate complexes of organoboronic acids.

Authors:  Yasunori Yamamoto; Miho Takizawa; Xiao-Qiang Yu; Norio Miyaura
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336
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  8 in total

1.  Synthesis of aryl sulfonamides via palladium-catalyzed chlorosulfonylation of arylboronic acids.

Authors:  J Robb DeBergh; Nootaree Niljianskul; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2013-07-12       Impact factor: 15.419

2.  Diastereoselective Oxidative C-N/C-O and C-N/C-N Bond Formation Tandems Initiated by Visible Light: Synthesis of Fused N-Arylindolines.

Authors:  Scott A Morris; Theresa H Nguyen; Nan Zheng
Journal:  Adv Synth Catal       Date:  2015-07-14       Impact factor: 5.837

3.  Heteroaryl-Heteroaryl, Suzuki-Miyaura, Anhydrous Cross-Coupling Reactions Enabled by Trimethyl Borate.

Authors:  Vincent M Kassel; Christopher M Hanneman; Connor P Delaney; Scott E Denmark
Journal:  J Am Chem Soc       Date:  2021-08-20       Impact factor: 16.383

4.  Investigating the dearomative rearrangement of biaryl phosphine-ligated Pd(II) complexes.

Authors:  Phillip J Milner; Thomas J Maimone; Mingjuan Su; Jiahao Chen; Peter Müller; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2012-11-27       Impact factor: 15.419

5.  Mild and general conditions for negishi cross-coupling enabled by the use of palladacycle precatalysts.

Authors:  Yang Yang; Nathan J Oldenhuis; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2012-11-22       Impact factor: 15.336

6.  Pd-Catalyzed Difluoromethylations of Aryl Boronic Acids, Halides, and Pseudohalides with ICF2 H Generated ex Situ.

Authors:  Oliver R Gedde; Andreas Bonde; Peter I Golbaekdal; Troels Skrydstrup
Journal:  Chemistry       Date:  2022-05-03       Impact factor: 5.020

7.  Enhancing Metalating Efficiency of the Sodium Amide NaTMP in Arene Borylation Applications.

Authors:  Leonie J Bole; Andreu Tortajada; Eva Hevia
Journal:  Angew Chem Int Ed Engl       Date:  2022-05-05       Impact factor: 16.823

8.  Use of N-methyliminodiacetic acid boronate esters in suzuki-miyaura cross-coupling polymerizations of triarylamine and fluorene monomers.

Authors:  Andrew B Foster; Viktor Bagutski; Josue I Ayuso-Carrillo; Martin J Humphries; Michael J Ingleson; Michael L Turner
Journal:  J Polym Sci A Polym Chem       Date:  2017-07-03       Impact factor: 2.702
  8 in total

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