Synthesis 2014; 46(16): 2143-2148
DOI: 10.1055/s-0033-1338659
practical synthetic procedures
© Georg Thieme Verlag Stuttgart · New York

Conversion of Aromatic Amino into Trifluoromethyl Groups through a Sandmeyer­-Type Transformation

Xi Wang
Beijing National Laboratory of Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, P. R. of China   Fax: +86(10)62751708   Email: [email protected]
,
Yan Xu
Beijing National Laboratory of Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, P. R. of China   Fax: +86(10)62751708   Email: [email protected]
,
Yujing Zhou
Beijing National Laboratory of Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, P. R. of China   Fax: +86(10)62751708   Email: [email protected]
,
Yan Zhang
Beijing National Laboratory of Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, P. R. of China   Fax: +86(10)62751708   Email: [email protected]
,
Jianbo Wang*
Beijing National Laboratory of Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, P. R. of China   Fax: +86(10)62751708   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 18 March 2014

Accepted after revision: 12 June 2014

Publication Date:
24 July 2014 (online)


Abstract

A novel strategy for aromatic trifluoromethylation by converting amino into trifluoromethyl groups via a Sandmeyer-type reaction is reported. The transformation involves diazotization of the aromatic amines with tert-butyl nitrite and hydrochloric acid to form aryldiazonium chlorides, followed by trifluoromethylation with trifluoromethylsilver at low temperature. Various readily available aromatic amines are smoothly converted under mild conditions.

Supporting Information

 
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