Literature DB >> 24117395

Copper-catalyzed decarboxylative trifluoromethylation of allylic bromodifluoroacetates.

Brett R Ambler1, Ryan A Altman.   

Abstract

The development of new synthetic fluorination reactions has important implications in medicinal, agricultural, and materials chemistries. Given the prevalence and accessibility of alcohols, methods to convert alcohols to trifluoromethanes are desirable. However, this transformation typically requires four-step processes, specialty chemicals, and/or stoichiometric metals to access the trifluoromethyl-containing product. A two-step copper-catalyzed decarboxylative protocol for converting allylic alcohols to trifluoromethanes is reported. Preliminary mechanistic studies distinguish this reaction from previously reported Cu-mediated reactions.

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Year:  2013        PMID: 24117395      PMCID: PMC3867938          DOI: 10.1021/ol402780k

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


  14 in total

1.  Practical synthesis of Boc-protected cis-4-trifluoromethyl and cis-4-difluoromethyl-L- prolines.

Authors:  Xiao-Long Qiu; Feng-Ling Qing
Journal:  J Org Chem       Date:  2002-10-04       Impact factor: 4.354

2.  Copper-catalyzed trifluoromethylation of allylsilanes.

Authors:  Ryo Shimizu; Hiromichi Egami; Yoshitaka Hamashima; Mikiko Sodeoka
Journal:  Angew Chem Int Ed Engl       Date:  2012-03-30       Impact factor: 15.336

Review 3.  Transition metal-catalyzed fluorination of multi carbon-carbon bonds: new strategies for fluorinated heterocycles.

Authors:  Guosheng Liu
Journal:  Org Biomol Chem       Date:  2012-06-26       Impact factor: 3.876

4.  Introduction of fluorine and fluorine-containing functional groups.

Authors:  Theresa Liang; Constanze N Neumann; Tobias Ritter
Journal:  Angew Chem Int Ed Engl       Date:  2013-07-19       Impact factor: 15.336

5.  Stereoselective synthesis of Boc-protected cis and trans-4-trifluoromethylprolines by asymmetric hydrogenation reactions.

Authors:  Juan R Del Valle; Murray Goodman
Journal:  Angew Chem Int Ed Engl       Date:  2002-05-03       Impact factor: 15.336

6.  Diamine Ligands in Copper-Catalyzed Reactions.

Authors:  David S Surry; Stephen L Buchwald
Journal:  Chem Sci       Date:  2010       Impact factor: 9.825

Review 7.  Transition metal catalysis and nucleophilic fluorination.

Authors:  Charlotte Hollingworth; Véronique Gouverneur
Journal:  Chem Commun (Camb)       Date:  2012-02-15       Impact factor: 6.222

8.  Enantioselective hydrogenation of allylphthalimides: an efficient method for the synthesis of beta-methyl chiral amines.

Authors:  Chun-Jiang Wang; Xianfeng Sun; Xumu Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2005-08-05       Impact factor: 15.336

9.  Synthesis of new fluorinated Tebufenpyrad analogs with acaricidal activity through regioselective pyrazole formation.

Authors:  Santos Fustero; Raquel Román; Juan F Sanz-Cervera; Antonio Simón-Fuentes; Jorge Bueno; Salvador Villanova
Journal:  J Org Chem       Date:  2008-10-15       Impact factor: 4.354

10.  Synthesis and antiviral evaluation of 2'-deoxy-2'-C-trifiuoromethyl beta-D-ribonucleoside analogues bearing the five naturally occurring nucleic acid bases.

Authors:  Frédéric Jeannot; Gilles Gosselin; Christophe Mathé
Journal:  Org Biomol Chem       Date:  2003-06-21       Impact factor: 3.876

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  9 in total

1.  Metal-catalyzed Decarboxylative Fluoroalkylation Reactions.

Authors:  Brett R Ambler; Ming-Hsiu Yang; Ryan A Altman
Journal:  Synlett       Date:  2016-12       Impact factor: 2.454

2.  An Unconventional Mechanistic Insight into SCF3 Formation from Difluorocarbene: Preparation of 18 F-Labeled α-SCF3 Carbonyl Compounds.

Authors:  Jian Zheng; Ran Cheng; Jin-Hong Lin; Dong-Hai Yu; Longle Ma; Lina Jia; Lan Zhang; Lu Wang; Ji-Chang Xiao; Steven H Liang
Journal:  Angew Chem Int Ed Engl       Date:  2017-02-14       Impact factor: 15.336

3.  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

4.  Ligand-controlled regiodivergent palladium-catalyzed decarboxylative allylation reaction to access α,α-difluoroketones.

Authors:  Ming-Hsiu Yang; Douglas L Orsi; Ryan A Altman
Journal:  Angew Chem Int Ed Engl       Date:  2015-01-07       Impact factor: 15.336

Review 5.  Decarboxylative fluorination strategies for accessing medicinally- relevant products.

Authors:  Yupu Qiao; Lingui Zhu; Brett R Ambler; Ryan A Altman
Journal:  Curr Top Med Chem       Date:  2014       Impact factor: 3.295

6.  Copper-Catalyzed Decarboxylative Trifluoromethylation of Propargyl Bromodifluoroacetates.

Authors:  Brett R Ambler; Santosh Peddi; Ryan A Altman
Journal:  Synthesis (Stuttg)       Date:  2014-07-15       Impact factor: 3.157

7.  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

8.  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

9.  Interrupting the Barton-McCombie Reaction: Aqueous Deoxygenative Trifluoromethylation of O-Alkyl Thiocarbonates.

Authors:  Zhi-Yun Liu; Silas P Cook
Journal:  Org Lett       Date:  2021-01-14       Impact factor: 6.072

  9 in total

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