TsNBr2 mediated oxidative functionalization of alkynes

A new approach has been developed for oxidative transformation of alkynes by controlled manipulation of TsNBr2 mediated process. Alkynes could be readily converted to ketones and α-bromoketones via an oxybromination–debromination sequence. When alkynes are treated successively with TsNBr2, KI and Na...

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Bibliographic Details
Published in:Tetrahedron 2016-07, Vol.72 (29), p.4151-4158
Main Authors: Rajbongshi, Kamal Krishna, Hazarika, Debojit, Phukan, Prodeep
Format: Article
Language:English
Subjects:
1-Bromoalkyne
Alkyne
Ketone
TsNBr2
α-Bromoketone
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Summary:A new approach has been developed for oxidative transformation of alkynes by controlled manipulation of TsNBr2 mediated process. Alkynes could be readily converted to ketones and α-bromoketones via an oxybromination–debromination sequence. When alkynes are treated successively with TsNBr2, KI and Na2SO3 in a mixture of acetone and water at room temperature, corresponding ketones were obtained. On the other hand, treatment of alkynes with TsNBr2 and Na2SO3 in a mixture of ethyl acetate, acetone and water at room temperature could produce corresponding α-bromoketones. 1-Bromoalkynes could also be synthesized from corresponding alkynes within a very short time using TsNBr2 at room temperature. In all cases, excellent yields of corresponding products are obtained. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2016.05.017