Regioselective Hydroiodination of Alkynes by in situ‐Generated HI

An efficient and highly selective hydroiodination of alkynes has been reported. The reaction utilizes in situ‐generated HI from [Rh]‐complex, molecular hydrogen, and iodine under ambient temperature. The methodology provided the Markovnikov products exclusively from terminal alkynes, and predominate...

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Bibliographic Details
Published in:Asian journal of organic chemistry 2020-01, Vol.9 (1), p.73-76
Main Authors: Li, Jiayan, Devi Laishram, Ronibala, Chen, Jingchao, Xu, Dandan, Shi, Guangrui, Lv, Haiping, Fan, Ruifeng, Fan, Baomin
Format: Article
Language:English
Subjects:
Alkynes
Ambient temperature
Hydroiodination
Iodine
Isomers
Molecular hydrogen
Molecular iodine
Organic chemistry
Vinyl iodides
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Summary:An efficient and highly selective hydroiodination of alkynes has been reported. The reaction utilizes in situ‐generated HI from [Rh]‐complex, molecular hydrogen, and iodine under ambient temperature. The methodology provided the Markovnikov products exclusively from terminal alkynes, and predominately E‐isomers from the internal alkynes in good yields. The reaction could be performed on a gram‐scale with good yield. Works on a gram scale too! An efficient and highly selective hydroiodination of alkynes utilizing in situ‐generated HI from [Rh]‐complex, molecular hydrogen, and iodine under ambient temperature has been developed. This methodology tolerates alkyl‐, aryl‐ and heteroaryl substituents on the alkyne moiety affording the Markovnikov products exclusively from terminal alkynes, and predominately E‐isomers from the internal alkynes in good yields.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.201900677