期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 53, 期 50, 页码 13880-13884出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201408121
关键词
alkynes; chlorothiolation; iron; radical reactions; synthetic methods
资金
- JSPS [26810060]
- MEXT program for promoting the enhancement of research universities
- Grants-in-Aid for Scientific Research [26810060] Funding Source: KAKEN
The radical addition of the ClS sigma-bond in sulfenyl chlorides to various CC triple bonds has been achieved with excellent regio- and stereoselectivity in the presence of a catalytic amount of a common iron salt. The reaction is compatible with a variety of functional groups and can be scaled up to the gram-scale with no loss in yield. As well as terminal alkynes, internal alkynes underwent stereodefined chlorothiolation to provide tetrasubstituted alkynes. Preliminary mechanistic investigations revealed a plausible radical process involving a sulfur-centered radical intermediate via iron-mediated homolysis of the ClS bond. The resulting chlorothiolation adducts can be readily transformed to the structurally complex alkenyl sulfides by cross-coupling reactions. The present reaction can also be applied to the complementary synthesis of the potentially useful bis-sulfoxide ligands for transition-metal-catalyzed reactions.
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