Literature DB >> 20481486

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

Gary A Molander1, Jessica Raushel, Noel M Ellis.   

Abstract

A uniquely stable acyl potassium trifluoroborate, potassium (2-phenylacetyl)trifluoroborate, has been synthesized and isolated. In the presence of an activating Lewis acid, this reagent reacts with azides to form amides in good yields.

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Year:  2010        PMID： 20481486      PMCID： PMC2896291          DOI： 10.1021/jo1004058

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


  8 in total

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Authors:  Tamio Hayashi; Kaori Yamasaki
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2.  Organotrifluoroborates: protected boronic acids that expand the versatility of the Suzuki coupling reaction.

Authors:  Gary A Molander; Noel Ellis
Journal:  Acc Chem Res       Date:  2007-01-26       Impact factor: 22.384

3.  Synthesis, structure of borylmagnesium, and its reaction with benzaldehyde to form benzoylborane.

Authors:  Makoto Yamashita; Yuta Suzuki; Yasutomo Segawa; Kyoko Nozaki
Journal:  J Am Chem Soc       Date:  2007-07-14       Impact factor: 15.419

4.  A new synthesis of butadienyl- and styrylboronic esters: highly reactive intermediates for Suzuki cross-coupling.

Authors:  Paolo Balma Tivola; Annamaria Deagostino; Cristina Prandi; Paolo Venturello
Journal:  Org Lett       Date:  2002-04-18       Impact factor: 6.005

5.  Development of the suzuki-miyaura cross-coupling reaction: use of air-stable potassium alkynyltrifluoroborates in aryl alkynylations.

Authors:  Gary A Molander; Bryson W Katona; Fouzia Machrouhi
Journal:  J Org Chem       Date:  2002-11-29       Impact factor: 4.354

6.  Asymmetric alkyldifluoroboranes and their use in secondary amine synthesis.

Authors:  Donald S Matteson; Gyung Youn Kim
Journal:  Org Lett       Date:  2002-06-27       Impact factor: 6.005

7.  Preparation of a stable trifluoroborate salt for the synthesis of 1-aryl-2,2-difluoro-enolethers and/or 2,2-difluoro-1-aryl-ketones via palladium-mediated cross-coupling.

Authors:  Jason D Katz; Blair T Lapointe; Christopher J Dinsmore
Journal:  J Org Chem       Date:  2009-11-20       Impact factor: 4.354

8.  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
  8 in total
  9 in total

1.  Amide-forming ligation of acyltrifluoroborates and hydroxylamines in water.

Authors:  Aaron M Dumas; Gary A Molander; Jeffrey W Bode
Journal:  Angew Chem Int Ed Engl       Date:  2012-04-26       Impact factor: 15.336

2.  Metal-free chlorodeboronation of organotrifluoroborates.

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

3.  Oxidation of organotrifluoroborates via oxone.

Authors:  Gary A Molander; Livia N Cavalcanti
Journal:  J Org Chem       Date:  2010-12-30       Impact factor: 4.354

4.  Copper-mediated N-Arylation of Methyl 2-Aminothiophene-3-carboxylate with Organoboron Reagents.

Authors:  Komal Rizwan; Idris Karakaya; Drew Heitz; Muhammad Zubair; Nasir Rasool; Gary A Molander
Journal:  Tetrahedron Lett       Date:  2015-12-09       Impact factor: 2.415

Review 5.  Methods to Make Homogenous Antibody Drug Conjugates.

Authors:  Toni Kline; Alexander R Steiner; Kalyani Penta; Aaron K Sato; Trevor J Hallam; Gang Yin
Journal:  Pharm Res       Date:  2014-12-16       Impact factor: 4.200

6.  Synthesis and stabilities of peptide-based [1]rotaxanes: molecular grafting onto lasso peptide scaffolds.

Authors:  Fumito Saito; Jeffrey W Bode
Journal:  Chem Sci       Date:  2017-01-26       Impact factor: 9.825

7.  A modular and concise approach to MIDA acylboronates via chemoselective oxidation of unsymmetrical geminal diborylalkanes: unlocking access to a novel class of acylborons.

Authors:  Shengjia Lin; Lucia Wang; Negin Aminoleslami; Yanting Lao; Chelsea Yagel; Abhishek Sharma
Journal:  Chem Sci       Date:  2019-03-21       Impact factor: 9.825

8.  Copper-Catalyzed Borylation of Acyl Chlorides with an Alkoxy Diboron Reagent: A Facile Route to Acylboron Compounds.

Authors:  Xiaolei Zhang; Alexandra Friedrich; Todd B Marder
Journal:  Chemistry       Date:  2022-06-13       Impact factor: 5.020

9.  Synthesis of secondary and tertiary amides without coupling agents from amines and potassium acyltrifluoroborates (KATs).

Authors:  Anne Schuhmacher; Tomoya Shiro; Sarah J Ryan; Jeffrey W Bode
Journal:  Chem Sci       Date:  2020-03-10       Impact factor: 9.825
  9 in total

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