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Literature DB >> 19105735

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

Gary A Molander¹, Belgin Canturk, Lauren E Kennedy.

Abstract

A wide variety of bench-stable potassium heteroaryltrifluoroborates were prepared, and general reaction conditions were developed for their cross-coupling to aryl and heteroaryl halides. The cross-coupled products were obtained in good to excellent yields. This method represents an efficient and facile installation of heterocyclic building blocks onto preexisting organic substructures.

Entities: Chemical Disease Gene

Mesh：

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Year: 2009 PMID： 19105735 PMCID： PMC2664078 DOI： 10.1021/jo802590b

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

33 in total

Review 1. Practical methodologies for the synthesis of indoles.

Authors: Guy R Humphrey; Jeffrey T Kuethe
Journal: Chem Rev Date: 2006-07 Impact factor: 60.622

2. New air-stable catalysts for general and efficient suzuki-miyaura cross-coupling reactions of heteroaryl chlorides.

Authors: Anil S Guram; Anthony O King; John G Allen; Xianghong Wang; Laurie B Schenkel; Johann Chan; Emilio E Bunel; Margaret M Faul; Robert D Larsen; Michael J Martinelli; Paul J Reider
Journal: Org Lett Date: 2006-04-27 Impact factor: 6.005

3. Ligand-free Pd/C-catalyzed Suzuki-Miyaura coupling reaction for the synthesis of heterobiaryl derivatives.

Authors: Yoshiaki Kitamura; Satoko Sako; Takahiro Udzu; Azusa Tsutsui; Tomohiro Maegawa; Yasunari Monguchi; Hironao Sajiki
Journal: Chem Commun (Camb) Date: 2007-10-02 Impact factor: 6.222

Review 4. Potassium organotrifluoroborates: new perspectives in organic synthesis.

Authors: Sylvain Darses; Jean-Pierre Genet
Journal: Chem Rev Date: 2007-12-21 Impact factor: 60.622

5. 2-Aryl-N-acyl indole derivatives as liver X receptor (LXR) agonists.

Authors: Sunil Kher; Kirk Lake; Ila Sircar; Madhavi Pannala; Farid Bakir; James Zapf; Kui Xu; Shao-Hui Zhang; Juping Liu; Lisa Morera; Naoki Sakurai; Rick Jack; Jie-Fei Cheng
Journal: Bioorg Med Chem Lett Date: 2007-06-10 Impact factor: 2.823

6. Catalysts for Suzuki-Miyaura coupling processes: scope and studies of the effect of ligand structure.

Authors: Timothy E Barder; Shawn D Walker; Joseph R Martinelli; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2005-04-06 Impact factor: 15.419

7. Palladium-catalyzed cross-coupling reactions of pyridylboronic acids with heteroaryl halides bearing a primary amine group: synthesis of highly substituted bipyridines and pyrazinopyridines.

Authors: Amy E Thompson; Gregory Hughes; Andrei S Batsanov; Martin R Bryce; Paul R Parry; Brian Tarbit
Journal: J Org Chem Date: 2005-01-07 Impact factor: 4.354

8. Arylboronic acids and arylpinacolboronate esters in Suzuki coupling reactions involving indoles. Partner role swapping and heterocycle protection.

Authors: Monica Prieto; Esther Zurita; Esmeralda Rosa; Lourdes Muñoz; Paul Lloyd-Williams; Ernest Giralt
Journal: J Org Chem Date: 2004-10-01 Impact factor: 4.354

9. 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

10. Highly efficient Suzuki-Miyaura coupling of heterocyclic substrates through rational reaction design.

Authors: Christoph A Fleckenstein; Herbert Plenio
Journal: Chemistry Date: 2008 Impact factor: 5.236

42 in total

1. Synthesis and reactivity of solid-supported organotrifluoroborates in Suzuki cross-coupling.

Authors: Virginie Colombel; Marc Presset; Daniel Oehlrich; Frederik Rombouts; Gary A Molander
Journal: Org Lett Date: 2012-03-09 Impact factor: 6.005

2. Synthesis of amidomethyltrifluoroborates and their use in cross-coupling reactions.

Authors: Gary A Molander; Marie-Aude Hiebel
Journal: Org Lett Date: 2010-11-05 Impact factor: 6.005

3. Nickel-catalyzed cross-coupling of potassium aryl- and heteroaryltrifluoroborates with unactivated alkyl halides.

Authors: Gary A Molander; O Andreea Argintaru; Ioana Aron; Spencer D Dreher
Journal: Org Lett Date: 2010-11-19 Impact factor: 6.005

4. Metal-free chlorodeboronation of organotrifluoroborates.

Authors: Gary A Molander; Livia N Cavalcanti
Journal: J Org Chem Date: 2011-08-03 Impact factor: 4.354

5. Synthesis of an acyltrifluoroborate and its fusion with azides to form amides.

Authors: Gary A Molander; Jessica Raushel; Noel M Ellis
Journal: J Org Chem Date: 2010-06-18 Impact factor: 4.354

6. Nonsymmetrical Bis-Azine Biaryls from Chloroazines: A Strategy Using Phosphorus Ligand-Coupling.

Authors: Benjamin T Boyle; Michael C Hilton; Andrew McNally
Journal: J Am Chem Soc Date: 2019-09-16 Impact factor: 15.419

7. From imide to lactam metallo-pyridocarbazoles: distinct scaffolds for the design of selective protein kinase inhibitors.

Authors: Nicholas Pagano; Eric Y Wong; Tom Breiding; Haidong Liu; Alexander Wilbuer; Howard Bregman; Qi Shen; Scott L Diamond; Eric Meggers
Journal: J Org Chem Date: 2009-12-04 Impact factor: 4.354

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

Authors: Gary A Molander; Sarah L J Trice; Brittany Tschaen
Journal: Tetrahedron Date: 2015-09-02 Impact factor: 2.457

9. Condensation reactions to form oxazoline-substituted potassium organotrifluoroborates.

Authors: Gary A Molander; Wilma Febo-Ayala; Ludivine Jean-Gérard
Journal: Org Lett Date: 2009-09-03 Impact factor: 6.005

10. 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