Literature DB >> 21405049

Reinvestigation of aminomethyltrifluoroborates and their application in Suzuki-Miyaura cross-coupling reactions.

Jessica Raushel1, Deidre L Sandrock, Kanth V Josyula, Deborah Pakyz, Gary A Molander.   

Abstract

A reinvestigation into the chemical composition of potassium aminomethyltrifluoroborates is reported. These n class="Chemical">trifluoroborato salts have been reassigned as zwitterionic ammoniomethyltrifluoroborates. Minor adjustments to the previously disclosed reaction conditions are reported that permit a similar level of activity as nucleophiles in Suzuki-Miyaura cross-coupling reactions.

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Year:  2011        PMID: 21405049      PMCID: PMC3074569          DOI: 10.1021/jo2001066

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


  7 in total

1.  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

2.  Synthesis of an anti-methicillin-resistant Staphylococcus aureus (MRSA) carbapenem via stannatrane-mediated Stille coupling.

Authors:  M S Jensen; C Yang; Y Hsiao; N Rivera; K M Wells; J Y Chung; N Yasuda; D L Hughes; P J Reider
Journal:  Org Lett       Date:  2000-04-20       Impact factor: 6.005

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

5.  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

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

Authors:  Gary A Molander; Belgin Canturk
Journal:  Org Lett       Date:  2008-04-26       Impact factor: 6.005

7.  Aminomethylations via cross-coupling of potassium organotrifluoroborates with aryl bromides.

Authors:  Gary A Molander; Deidre L Sandrock
Journal:  Org Lett       Date:  2007-03-17       Impact factor: 6.005

  7 in total
  7 in total

1.  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

2.  Suzuki-Miyaura cross-coupling of potassium trifluoro(N-methylheteroaryl)borates with aryl and heteroaryl halides.

Authors:  Gary A Molander; DaWeon Ryu; Mona Hosseini-Sarvari; Rammohan Devulapally; Dave G Seapy
Journal:  J Org Chem       Date:  2013-06-25       Impact factor: 4.354

3.  Aminomethylation of Aryl Halides using α-Silylamines Enabled by Ni/Photoredox Dual Catalysis.

Authors:  Camille Remeur; Christopher B Kelly; Niki R Patel; Gary A Molander
Journal:  ACS Catal       Date:  2017-08-16       Impact factor: 13.084

4.  Rapid and efficient access to secondary arylmethylamines.

Authors:  Nicolas Fleury-Brégeot; Jessica Raushel; Deidre L Sandrock; Spencer D Dreher; Gary A Molander
Journal:  Chemistry       Date:  2012-07-05       Impact factor: 5.236

5.  Synthesis and cross-coupling reactions of imidomethyltrifluoroborates with aryl chlorides.

Authors:  Rammohan Devulapally; Nicolas Fleury-Brégeot; Gary A Molander; Dave G Seapy
Journal:  Tetrahedron Lett       Date:  2012-02-29       Impact factor: 2.415

6.  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

7.  Facile synthesis of α-aminoboronic acids from amines and potassium acyltrifluoroborates (KATs) via trifluoroborate-iminiums (TIMs).

Authors:  Tomoya Shiro; Anne Schuhmacher; Moritz K Jackl; Jeffrey W Bode
Journal:  Chem Sci       Date:  2018-05-16       Impact factor: 9.825

  7 in total

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