Literature DB >> 22931498

Potassium Boc-protected secondary aminomethyltrifluoroborates: synthesis and Suzuki-Miyaura cross-coupling reactions.

Gary A Molander1, Inji Shin.   

Abstract

Seven potassium Boc-protected secondary aminomethyltrifluoroborates were prepared in a standardized two-step process. The Suzuki-Miyaura cross-coupling reaction was studied with this new class of nucleophiles, and a large variety of aryl and hetaryl chlorides provided the desired products in good to excellent yields, thereby allowing easy access to secondary aminomethyl substructures.

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Year:  2012        PMID： 22931498      PMCID： PMC3447629          DOI： 10.1021/ol301955s

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


  12 in total

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

Authors:  Gary A Molander; Marie-Aude Hiebel
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4.  Synthesis and Suzuki-Miyaura cross-coupling reactions of potassium Boc-protected aminomethyltrifluoroborate with aryl and hetaryl halides.

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

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6.  A new palladium precatalyst allows for the fast Suzuki-Miyaura coupling reactions of unstable polyfluorophenyl and 2-heteroaryl boronic acids.

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7.  Rapid and efficient access to secondary arylmethylamines.

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Journal:  Chemistry       Date:  2012-07-05       Impact factor: 5.236

8.  Suzuki-Miyaura cross-coupling reactions of potassium Boc-protected aminomethyltrifluoroborate with aryl and hetaryl mesylates.

Authors:  Gary A Molander; Inji Shin
Journal:  Org Lett       Date:  2012-05-31       Impact factor: 6.005

9.  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

10.  A study of the effect on nucleophilic hydrolytic activity of pancreatic elastase, trypsin, chymotrypsin, and leucine aminopeptidase by boronic acids in the presence of arabinogalactan: a subsequent study on the hydrolytic activity of chymotrypsin by boronic acids in the presence of mono-, di-, and trisaccharides.

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  7 in total

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Authors:  Shinya Adachi; Armand B Cognetta; Micah J Niphakis; Zhi He; Adam Zajdlik; Jeffrey D St Denis; Conor C G Scully; Benjamin F Cravatt; Andrei K Yudin
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2.  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
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3.  Synthesis of Secondary and Tertiary Alkylboranes via Formal Hydroboration of Terminal and 1,1-Disubstituted Alkenes.

Authors:  Hilary A Kerchner; John Montgomery
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4.  α-Arylation/Heteroarylation of Chiral α-Aminomethyltrifluoroborates by Synergistic Iridium Photoredox/Nickel Cross-Coupling Catalysis.

Authors:  Mirna El Khatib; Ricardo Augusto Massarico Serafim; Gary A Molander
Journal:  Angew Chem Int Ed Engl       Date:  2015-11-23       Impact factor: 15.336

5.  Pd-catalyzed Suzuki-Miyaura cross-coupling reactions between sulfamates and potassium Boc-protected aminomethyltrifluoroborates.

Authors:  Gary A Molander; Inji Shin
Journal:  Org Lett       Date:  2013-05-06       Impact factor: 6.005

6.  Accessing Aliphatic Amines in C-C Cross-Couplings by Visible Light/Nickel Dual Catalysis.

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Review 7.  Recent Advances in Photoredox-Mediated Radical Conjugate Addition Reactions: An Expanding Toolkit for the Giese Reaction.

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Journal:  Angew Chem Int Ed Engl       Date:  2021-07-21       Impact factor: 16.823
  7 in total

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