Literature DB >> 18759480

Cross-coupling of cyclopropyl- and cyclobutyltrifluoroborates with aryl and heteroaryl chlorides.

Gary A Molander1, Paul E Gormisky.   

Abstract

Suitable conditions were found for the Suzuki-Miyaura cross-coupling reaction of potassium cyclopropyl- and cyclobutyltrifluoroborates with aryl chlorides. Both of these secondary alkyl trifluoroborates coupled in moderate to excellent yield with electron-rich, electron-poor, and hindered aryl chlorides to give a variety of substituted aryl cyclopropanes and cyclobutanes.

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Year:  2008        PMID： 18759480      PMCID： PMC2635095          DOI： 10.1021/jo801269m

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


  17 in total

Review 1.  Biosynthesis and metabolism of cyclopropane rings in natural compounds.

Authors:  Ludger A Wessjohann; Wolfgang Brandt; Thies Thiemann
Journal:  Chem Rev       Date:  2003-04       Impact factor: 60.622

Review 2.  The combinatorial synthesis of bicyclic privileged structures or privileged substructures.

Authors:  Douglas A Horton; Gregory T Bourne; Mark L Smythe
Journal:  Chem Rev       Date:  2003-03       Impact factor: 60.622

3.  An extremely active catalyst for the Negishi cross-coupling reaction.

Authors:  Jacqueline E Milne; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2004-10-13       Impact factor: 15.419

4.  The B-Alkyl Suzuki-Miyaura Cross-Coupling Reaction: Development, Mechanistic Study, and Applications in Natural Product Synthesis A list of abbreviations can be found at the end of the article.

Authors:  Sherry R. Chemler; Dirk Trauner; Samuel J. Danishefsky
Journal:  Angew Chem Int Ed Engl       Date:  2001-12-17       Impact factor: 15.336

5.  Direct N-cyclopropylation of cyclic amides and azoles employing a cyclopropylbismuth reagent.

Authors:  Alexandre Gagnon; Miguel St-Onge; Kelly Little; Martin Duplessis; Francis Barabé
Journal:  J Am Chem Soc       Date:  2007-01-10       Impact factor: 15.419

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 alkylation of sp2 and sp3 C-H bonds with methylboroxine and alkylboronic acids: two distinct C-H activation pathways.

Authors:  Xiao Chen; Charles E Goodhue; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2006-10-04       Impact factor: 15.419

8.  Catalytic enantioselective hydroboration of cyclopropenes.

Authors:  Marina Rubina; Michael Rubin; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2003-06-18       Impact factor: 15.419

9.  Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of potassium aryl- and heteroaryltrifluoroborates.

Authors:  Gary A Molander; Betina Biolatto
Journal:  J Org Chem       Date:  2003-05-30       Impact factor: 4.354

10.  Palladium-catalyzed cross-coupling of stereospecific potassium cyclopropyl trifluoroborates with aryl bromides.

Authors:  Guo-Hua Fang; Zheng-Jun Yan; Min-Zhi Deng
Journal:  Org Lett       Date:  2004-02-05       Impact factor: 6.005
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  12 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.  Cross-coupling of mesylated phenol derivatives with potassium cyclopropyltrifluoroborate.

Authors:  Gary A Molander; Floriane Beaumard; Terren K Niethamer
Journal:  J Org Chem       Date:  2011-09-02       Impact factor: 4.354

3.  Single-electron transmetalation: an enabling technology for secondary alkylboron cross-coupling.

Authors:  David N Primer; Idris Karakaya; John C Tellis; Gary A Molander
Journal:  J Am Chem Soc       Date:  2015-02-04       Impact factor: 15.419

4.  Suzuki-Miyaura cross-coupling reactions of primary alkyltrifluoroborates with aryl chlorides.

Authors:  Spencer D Dreher; Siang-Ee Lim; Deidre L Sandrock; Gary A Molander
Journal:  J Org Chem       Date:  2009-05-15       Impact factor: 4.354

5.  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

6.  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

Review 7.  Potassium trifluoroborate salts as convenient, stable reagents for difficult alkyl transfers.

Authors:  Gary A Molander; Deidre L Sandrock
Journal:  Curr Opin Drug Discov Devel       Date:  2009-11

8.  Efficient C-B bond formation promoted by N-heterocyclic carbenes: synthesis of tertiary and quaternary B-substituted carbons through metal-free catalytic boron conjugate additions to cyclic and acyclic alpha,beta-unsaturated carbonyls.

Authors:  Kang-sang Lee; Adil R Zhugralin; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2009-06-03       Impact factor: 15.419

9.  Rapid access to diverse, trifluoromethyl-substituted alkenes using complementary strategies.

Authors:  James P Phelan; Rebecca J Wiles; Simon B Lang; Christopher B Kelly; Gary A Molander
Journal:  Chem Sci       Date:  2018-02-22       Impact factor: 9.825

10.  Cyclin-Dependent Kinase (CDK) Inhibitors: Structure-Activity Relationships and Insights into the CDK-2 Selectivity of 6-Substituted 2-Arylaminopurines.

Authors:  Christopher R Coxon; Elizabeth Anscombe; Suzannah J Harnor; Mathew P Martin; Benoit Carbain; Bernard T Golding; Ian R Hardcastle; Lisa K Harlow; Svitlana Korolchuk; Christopher J Matheson; David R Newell; Martin E M Noble; Mangaleswaran Sivaprakasam; Susan J Tudhope; David M Turner; Lan Z Wang; Stephen R Wedge; Christopher Wong; Roger J Griffin; Jane A Endicott; Céline Cano
Journal:  J Med Chem       Date:  2017-02-14       Impact factor: 7.446
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