TY - JOUR
T1 - Regio- And Stereoselective Hydroiodination of Internal Alkynes with Ex Situ-Generated HI
AU - Nozawa-Kumada, Kanako
AU - Noguchi, Koto
AU - Akada, Tomoya
AU - Shigeno, Masanori
AU - Kondo, Yoshinori
N1 - Funding Information:
This work was financially supported by Japan Society for the Promotion of Science (JSPS) KAKENHI Grants 19H03346 and 19K16309. This work was also supported by Grant for Basic Science Research Projects from the Takahashi Industrial and Economic Research Foundation, the Takeda Science Foundation, the TOBE MAKI Scholarship Foundation, the Kurata Grants from The Hitachi Global Foundation, the FUJIFILM Award in Synthetic Organic Chemistry, Japan, and the Platform Project for Supporting Drug Discovery and Life Science Research funded by the Japan Agency for Medical Research and Development (AMED).
Publisher Copyright:
© 2021 American Chemical Society.
PY - 2021/9/3
Y1 - 2021/9/3
N2 - Herein, we report an efficient and practical hydroiodination of internal alkynes using HI generated ex situ from the readily available triethylsilane and I2. This system offers high regio- and stereoselectivity to afford (E)-vinyl iodides in good yields under mild conditions. Furthermore, the hydroiodination reaction shows high functional group tolerance toward alkyl, methoxy, halogen, trifluoromethyl, cyano, ester, halomethyl, acid-sensitive silyl ether, and acetal moieties.
AB - Herein, we report an efficient and practical hydroiodination of internal alkynes using HI generated ex situ from the readily available triethylsilane and I2. This system offers high regio- and stereoselectivity to afford (E)-vinyl iodides in good yields under mild conditions. Furthermore, the hydroiodination reaction shows high functional group tolerance toward alkyl, methoxy, halogen, trifluoromethyl, cyano, ester, halomethyl, acid-sensitive silyl ether, and acetal moieties.
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U2 - 10.1021/acs.orglett.1c02218
DO - 10.1021/acs.orglett.1c02218
M3 - Article
C2 - 34474572
AN - SCOPUS:85114316743
VL - 23
SP - 6659
EP - 6663
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 17
ER -