Catalytic asymmetric radical aminoperfluoroalkylation and aminodifluoromethylation of alkenes to versatile enantioenriched-fluoroalkyl amines

Jin-Shun Lin, Fu-Li Wang, Xiao-Yang Dong, Wei-Wei He, Yue Yuan, Su Chen and Xin-Yuan Liu ()
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Jin-Shun Lin: South University of Science and Technology of China
Fu-Li Wang: South University of Science and Technology of China
Xiao-Yang Dong: South University of Science and Technology of China
Wei-Wei He: South University of Science and Technology of China
Yue Yuan: South University of Science and Technology of China
Su Chen: South University of Science and Technology of China
Xin-Yuan Liu: South University of Science and Technology of China

Nature Communications, 2017, vol. 8, issue 1, 1-11

Abstract: Abstract Although great success has been achieved in asymmetric fluoroalkylation reactions via nucleophilic or electrophilic processes, the development of asymmetric radical versions of this type of reactions remains a formidable challenge because of the involvement of highly reactive radical species. Here we report a catalytic asymmetric radical aminoperfluoroalkylation and aminodifluoromethylation of alkenes with commercially available fluoroalkylsulfonyl chlorides as the radical sources, providing a versatile platform to access four types of enantioenriched α-tertiary pyrrolidines bearing β-perfluorobutanyl, trifluoromethyl, difluoroacetyl and even difluoromethyl groups in excellent yields and with excellent enantioselectivity. The key to success is not only the introduction of the CuBr/chiral phosphoric acid dual-catalytic system but also the use of silver carbonate to suppress strong background and side hydroamination reactions caused by a stoichiometric amount of the in situ generated HCl. Broad substrate scope, excellent functional group tolerance and versatile functionalization of the products make this approach very practical and attractive.

Date: 2017
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DOI: 10.1038/ncomms14841

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