Literature DB >> 18439019

Preparation of potassium alkoxymethyltrifluoroborates and their cross-coupling with aryl chlorides.

Gary A Molander1, Belgin Canturk.   

Abstract

A wide variety of alkoxymethyltrifluoroborate substrates were prepared via SN2 displacement of potassium bromomethyltrifluoroborate with various alkoxides in excellent yields. These alkoxymethyltrifluoroborates were effectively cross-coupled with several aryl chlorides. This method provides a unique dissonant disconnect that allows greater flexibility in the design of new and improved synthetic pathways.

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Year:  2008        PMID： 18439019      PMCID： PMC4470619          DOI： 10.1021/ol800532p

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


  4 in total

1.  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

2.  Stereospecific cross-coupling of alpha-(thiocarbamoyl)organostannanes with alkenyl, aryl, and heteroaryl iodides.

Authors:  J R Falck; Paresh K Patel; Anish Bandyopadhyay
Journal:  J Am Chem Soc       Date:  2007-01-31       Impact factor: 15.419

3.  Synthesis of functionalized organotrifluoroborates via halomethyltrifluoroborates.

Authors:  Gary A Molander; Jungyeob Ham
Journal:  Org Lett       Date:  2006-05-11       Impact factor: 6.005

4.  Scope of aminomethylations via Suzuki-Miyaura cross-coupling of organotrifluoroborates.

Authors:  Gary A Molander; Paul E Gormisky; Deidre L Sandrock
Journal:  J Org Chem       Date:  2008-02-20       Impact factor: 4.354
  4 in total
  17 in total

1.  Metal-free chlorodeboronation of organotrifluoroborates.

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

2.  Cross-coupling of mesylated phenol derivatives with potassium alkoxymethyltrifluoroborates.

Authors:  Gary A Molander; Floriane Beaumard
Journal:  Org Lett       Date:  2011-07-06       Impact factor: 6.005

3.  Suzuki coupling of potassium cyclopropyl- and alkoxymethyltrifluoroborates with benzyl chlorides.

Authors:  Virginie Colombel; Frederik Rombouts; Daniel Oehlrich; Gary A Molander
Journal:  J Org Chem       Date:  2012-03-06       Impact factor: 4.354

4.  Synthesis and cross-coupling of sulfonamidomethyltrifluoroborates.

Authors:  Gary A Molander; Nicolas Fleury-Brégeot; Marie-Aude Hiebel
Journal:  Org Lett       Date:  2011-03-02       Impact factor: 6.005

5.  Negishi coupling of secondary alkylzinc halides with aryl bromides and chlorides.

Authors:  Chong Han; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2009-06-10       Impact factor: 15.419

6.  Orthogonal reactivity in boryl-substituted organotrifluoroborates.

Authors:  Gary A Molander; Deidre L Sandrock
Journal:  J Am Chem Soc       Date:  2008-11-26       Impact factor: 15.419

7.  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

8.  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 9.  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

10.  Scope of the Suzuki-Miyaura cross-coupling reaction of potassium trifluoroboratoketohomoenolates.

Authors:  Gary A Molander; Ludivine Jean-Gérard
Journal:  J Org Chem       Date:  2009-02-06       Impact factor: 4.354
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