Literature DB >> 25380504

Sandmeyer difluoromethylation of (hetero-)arenediazonium salts.

Christian Matheis1, Kévin Jouvin, Lukas J Goossen.   

Abstract

A Sandmeyer-type difluoromethylation process has been developed that allows the straightforward conversion of (hetero-)arenediazonium salts into the corresponding difluoromethyl (hetero-)arenes under mild conditions. The actual difluoromethylating reagent, a difluoromethyl-copper complex, is formed in situ from copper thiocyanate and TMS-CF2H. The diazonium salts are either preformed or generated in situ from broadly available aromatic amines.

Entities:  

Year:  2014        PMID： 25380504     DOI： 10.1021/ol5030037

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


  14 in total

1.  Chlorodifluoromethane-triggered formation of difluoromethylated arenes catalysed by palladium.

Authors:  Zhang Feng; Qiao-Qiao Min; Xia-Ping Fu; Lun An; Xingang Zhang
Journal:  Nat Chem       Date:  2017-03-14       Impact factor: 24.427

2.  Palladium-catalyzed intramolecular C-H difluoroalkylation: synthesis of substituted 3,3-difluoro-2-oxindoles.

Authors:  Shi-Liang Shi; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2014-12-04       Impact factor: 15.336

3.  Copper-Catalyzed Cyclopropanol Ring Opening Csp(3)-Csp(3) Cross-Couplings with (Fluoro)Alkyl Halides.

Authors:  Zhishi Ye; Kristen E Gettys; Xingyu Shen; Mingji Dai
Journal:  Org Lett       Date:  2015-12-04       Impact factor: 6.005

4.  Copper-catalyzed carbo-difluoromethylation of alkenes via radical relay.

Authors:  Aijie Cai; Wenhao Yan; Xiaojun Zeng; Samson B Zacate; Tzu-Hsuan Chao; Jeanette A Krause; Mu-Jeng Cheng; Wei Liu
Journal:  Nat Commun       Date:  2021-06-01       Impact factor: 14.919

5.  Palladium-catalyzed difluoromethylation of heteroaryl chlorides, bromides and iodides.

Authors:  Changhui Lu; Yang Gu; Jiang Wu; Yucheng Gu; Qilong Shen
Journal:  Chem Sci       Date:  2017-04-24       Impact factor: 9.825

6.  Mild and Regioselective Pd(OAc)2-Catalyzed C-H Arylation of Tryptophans by [ArN2]X, Promoted by Tosic Acid.

Authors:  Alan J Reay; L Anders Hammarback; Joshua T W Bray; Thomas Sheridan; David Turnbull; Adrian C Whitwood; Ian J S Fairlamb
Journal:  ACS Catal       Date:  2017-07-10       Impact factor: 13.084

7.  Difluoromethylation of (hetero)aryl chlorides with chlorodifluoromethane catalyzed by nickel.

Authors:  Chang Xu; Wen-Hao Guo; Xu He; Yin-Long Guo; Xue-Ying Zhang; Xingang Zhang
Journal:  Nat Commun       Date:  2018-03-21       Impact factor: 14.919

8.  Direct heterobenzylic fluorination, difluorination and trifluoromethylthiolation with dibenzenesulfonamide derivatives.

Authors:  Michael Meanwell; Bharani Shashank Adluri; Zheliang Yuan; Josiah Newton; Philippe Prevost; Matthew B Nodwell; Chadron M Friesen; Paul Schaffer; Rainer E Martin; Robert Britton
Journal:  Chem Sci       Date:  2018-06-07       Impact factor: 9.825

9.  Oxydifluoromethylation of Alkenes by Photoredox Catalysis: Simple Synthesis of CF2H-Containing Alcohols.

Authors:  Yusuke Arai; Ren Tomita; Gaku Ando; Takashi Koike; Munetaka Akita
Journal:  Chemistry       Date:  2015-12-16       Impact factor: 5.236

10.  Organophotoredox Hydrodefluorination of Trifluoromethylarenes with Translational Applicability to Drug Discovery.

Authors:  Jeroen B I Sap; Natan J W Straathof; Thomas Knauber; Claudio F Meyer; Maurice Médebielle; Laura Buglioni; Christophe Genicot; Andrés A Trabanco; Timothy Noël; Christopher W Am Ende; Véronique Gouverneur
Journal:  J Am Chem Soc       Date:  2020-05-11       Impact factor: 15.419
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