Catalytic Asymmetric Intermolecular Radical Aminotrifluoromethylation of Alkenes with Hydrazines by Cu(I)/CPA Cooperative Catalysis

Wang，Zhe1,2; Cheng，Jiang Tao3; Shi，Zhichao1,2; Wang，Na3; Zhan，Feng1,2; Jiang，Sheng Peng3; Lin，Jin Shun1,2; Jiang，Yuyang2,4; Liu，Xin Yuan3

2020

10.1002/cctc.202001398

ChemCatChem   影响因子和分区

1867-3880

1867-3899

A first catalytic enantioselective intermolecular radical aminotrifluoromethylation of alkene with hydrazine and Togni's reagent by Cu(I)/CPA cooperative catalysis has been reported, accessing diversely substituted CF-containing enantioenriched diarylmethylamines bearing an α-tertiary stereocenter with high enantioselectivity and excellent chemoselectivity. The highly asymmetric induction of C−N bond formation between hydrazine and the carbocation intermediate was achieved by using a CPA catalyst via hydrogen-bonding and ion pair interaction.

aminotrifluoromethylation asymmetric cooperative catalysis diarylmethylamine radical-involved

SCI ; EI

英语

其他

National Natural Science Foundation of China[21602098] ; Shenzhen Development and Reform Committee[2019156] ; Shenzhen Science, Technology and Innovation Commission[JCYJ20180306174248782] ; Department of Science and Technology of Guangdong Province[2017B030314083] ; Shenzhen Bay Laboratory Open Funding[SZBL2019062801009]

Chemistry

Chemistry, Physical

WOS:000573846600001

WILEY-V C H VERLAG GMBH

20204009291815

Olefins ; Copper compounds ; Catalysis ; Enantioselectivity ; Hydrogen bonds

Physical Chemistry:801.4 ; Chemical Reactions:802.2 ; Organic Compounds:804.1 ; Inorganic Compounds:804.2

2-s2.0-85091724970

Scopus

1.Department of Chemistry,Tsinghua University,Beijing,100084,China
2.The State Key Laboratory of Chemical Oncogenomics,Key Laboratory of Chemical Biology,Tsinghua Shenzhen International Graduate School,Shenzhen,518055,China
3.Shenzhen Grubbs Institute and Department of Chemistry,Guangdong Provincial Key Laboratory of Catalysis,Southern University of Science and Technology,Shenzhen,518055,China
4.School of Pharmaceutical Sciences,Tsinghua University,Beijing,100084,China

Wang，Zhe,Cheng，Jiang Tao,Shi，Zhichao,et al. Catalytic Asymmetric Intermolecular Radical Aminotrifluoromethylation of Alkenes with Hydrazines by Cu(I)/CPA Cooperative Catalysis[J]. ChemCatChem,2020,13(1):185-190.

Wang，Zhe.,Cheng，Jiang Tao.,Shi，Zhichao.,Wang，Na.,Zhan，Feng.,...&Liu，Xin Yuan.(2020).Catalytic Asymmetric Intermolecular Radical Aminotrifluoromethylation of Alkenes with Hydrazines by Cu(I)/CPA Cooperative Catalysis.ChemCatChem,13(1),185-190.

Wang，Zhe,et al."Catalytic Asymmetric Intermolecular Radical Aminotrifluoromethylation of Alkenes with Hydrazines by Cu(I)/CPA Cooperative Catalysis".ChemCatChem 13.1(2020):185-190.