Literature DB >> 28260839

Metal-catalyzed Decarboxylative Fluoroalkylation Reactions.

Brett R Ambler1, Ming-Hsiu Yang1, Ryan A Altman1.   

Abstract

Metal-catalyzed decarboxylative fluoroalkylation reactions enable the conversion of simple O-based substrates into biologically relevant fluorinated analogs. Herein, we present decarboxylative methods that facilitate the synthesis of trifluoromethyl- and difluoroketone-containing products. We highlight key mechanistic aspects that are critical for efficient catalysis, and that inspired our thinking while developing the reactions.

Entities:  

Keywords:  Catalysis; Copper; Decarboxylation; Difluoroketone; Fluorine; Palladium; Trifluoromethylation

Year:  2016        PMID： 28260839      PMCID： PMC5330304          DOI： 10.1055/s-0036-1588637

Source DB:  PubMed          Journal:  Synlett        ISSN： 0936-5214            Impact factor:   2.454


  37 in total

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Authors:  G. K. Surya Prakash; Andrei K. Yudin
Journal:  Chem Rev       Date:  1997-05-08       Impact factor: 60.622

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Authors:  Olivier Baudoin
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3.  Trifluoromethyltrimethylsilane: nucleophilic trifluoromethylation and beyond.

Authors:  Xiao Liu; Cong Xu; Mang Wang; Qun Liu
Journal:  Chem Rev       Date:  2014-04-22       Impact factor: 60.622

4.  Direct cupration of fluoroform.

Authors:  Alessandro Zanardi; Maxim A Novikov; Eddy Martin; Jordi Benet-Buchholz; Vladimir V Grushin
Journal:  J Am Chem Soc       Date:  2011-12-02       Impact factor: 15.419

5.  Copper-mediated trifluoromethylation of propargyl acetates leading to trifluoromethyl-allenes.

Authors:  Yun-Long Ji; Jun-Jie Kong; Jin-Hong Lin; Ji-Chang Xiao; Yu-Cheng Gu
Journal:  Org Biomol Chem       Date:  2014-05-14       Impact factor: 3.876

6.  Decarboxylative benzylations of alkynes and ketones.

Authors:  Robert R P Torregrosa; Yamuna Ariyarathna; Kalicharan Chattopadhyay; Jon A Tunge
Journal:  J Am Chem Soc       Date:  2010-07-14       Impact factor: 15.419

7.  Organocatalytic asymmetric synthesis of 3-difluoroalkyl 3-hydroxyoxindoles.

Authors:  Yun-Lin Liu; Jian Zhou
Journal:  Chem Commun (Camb)       Date:  2012-01-09       Impact factor: 6.222

8.  Ligand-Controlled Regioselective Copper-Catalyzed Trifluoromethylation To Generate (Trifluoromethyl)allenes.

Authors:  Brett R Ambler; Santosh Peddi; Ryan A Altman
Journal:  Org Lett       Date:  2015-04-24       Impact factor: 6.005

9.  Direct Access to α,α-Difluoroacylated Arenes by Palladium-Catalyzed Carbonylation of (Hetero)Aryl Boronic Acid Derivatives.

Authors:  Thomas L Andersen; Mette W Frederiksen; Katrine Domino; Troels Skrydstrup
Journal:  Angew Chem Int Ed Engl       Date:  2016-06-27       Impact factor: 15.336

10.  Copper-Catalyzed Synthesis of Trifluoroethylarenes from Benzylic Bromodifluoroacetates.

Authors:  Brett R Ambler; Lingui Zhu; Ryan A Altman
Journal:  J Org Chem       Date:  2015-08-11       Impact factor: 4.354
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  3 in total

1.  Catalytic One-Step Deoxytrifluoromethylation of Alcohols.

Authors:  Francisco de Azambuja; Sydney M Lovrien; Patrick Ross; Brett R Ambler; Ryan A Altman
Journal:  J Org Chem       Date:  2019-01-25       Impact factor: 4.354

2.  Nickel-Catalyzed Decarbonylative Synthesis of Fluoroalkyl Thioethers.

Authors:  Conor E Brigham; Christian A Malapit; Naish Lalloo; Melanie S Sanford
Journal:  ACS Catal       Date:  2020-07-17       Impact factor: 13.084

3.  Decarbonylative Fluoroalkylation at Palladium(II): From Fundamental Organometallic Studies to Catalysis.

Authors:  Naish Lalloo; Christian A Malapit; S Maryamdokht Taimoory; Conor E Brigham; Melanie S Sanford
Journal:  J Am Chem Soc       Date:  2021-10-28       Impact factor: 15.419
  3 in total

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