Silicon powder: the first nonmetal elemental catalyst for aminobromination of olefins with TsNH(2) and NBS

Silicon powder was found, for the first time, to be an efficient alternative to transition metal catalysts for aminobromination of alpha,beta-unsaturated carbonyl compounds and simple olefins with p-toluenesulfonamide (4-TsNH(2)) and NBS, affording the aminobrominated products in high yields and reg...

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Bibliographic Details
Published in:Organic letters 2009-09, Vol.11 (18), p.4216-4219
Main Authors: Wei, Jun-Fa, Chen, Zhan-Guo, Lei, Wei, Zhang, Li-Hui, Wang, Ming-Zheng, Shi, Xian-Ying, Li, Run-Tao
Format: Article
Language:English
Subjects:
Alkenes - chemistry
Bromine - chemistry
Catalysis
Combinatorial Chemistry Techniques
Powders - chemistry
Silicon - chemistry
Stereoisomerism
Sulfonamides - chemistry
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Summary:Silicon powder was found, for the first time, to be an efficient alternative to transition metal catalysts for aminobromination of alpha,beta-unsaturated carbonyl compounds and simple olefins with p-toluenesulfonamide (4-TsNH(2)) and NBS, affording the aminobrominated products in high yields and regio- and stereoselectivity. The high reactivity of electron-rich substrates reveals that the reaction has the electrophilic addition feature.
ISSN:1523-7052
DOI:10.1021/ol9015833