期刊
TETRAHEDRON
卷 74, 期 25, 页码 3129-3136出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2017.12.040
关键词
Pyridines; Diazines; C-S bonds; Heteroaryl thioethers; Phosphonium salts; Late-stage functionalization
资金
- Colorado State University
- gs2:ACS Petroleum Research Fund [ACS PRF56878-DNI1]
Heteroaryl thioethers, comprised of pyridines and diazines, are an important class of compounds with relevance to medicinal chemistry. Metal-catalyzed cross-couplings and SNAr reactions are traditionally used to form C-S bonds in these systems but are limited by available halogenated precursors. An alternative approach is presented where pyridines and diazines are transformed into heterocyclic phosphonium salts and then C-S bonds are formed by adding thiolate nucleophiles. The process is 4-selective for pyridines, simple to execute and can be used to make derivatives of complex pharmaceuticals. (C) 2017 Elsevier Ltd. All rights reserved.
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