Efficient one-pot transformation of aminoarenes to haloarenes using halodimethylisulfonium halides generated in situ

W Baik, W Luan, HJ Lee, CH Yoon…

Index: Baik, Woonphil; Luan, Wanqiang; Lee, Hyun Joo; Yoon, Cheol Hun; Koo, Sangho; Kim, Byeong Hyo Canadian Journal of Chemistry, 2005 , vol. 83, # 3 p. 213 - 219

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Citation Number: 36

Abstract

Halodimethylsulfonium halide 1, which is readily formed in situ from hydrohaloic acid and DMSO, is a good nucleophilic halide. This activated nucleophilic halide rapidly converts aryldiazonium salt prepared in situ by the same hydrohaloic acid and nitrite ion to aryl chlorides, bromides, or iodides in good yield. The combined action of nitrite ion and hydrohaloic acid in DMSO is required for the direct transformation of aromatic amines, ...