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Phosphine-Catalyzed Anti-Hydroboration of Internal Alkynes

Kazunori Nagao, Ayaka Yamazaki, Hirohisa Ohmiya* and Masaya Sawamura*

*Hokkaido University, Sapporo 060-0810; Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan, Email: ohmiyap.kanazawa-u.ac.jp, sawamurasci.hokudai.ac.jp

K. Nagao, A. Yamazaki, H. Ohmiya, M. Sawamura, Org. Lett., 2018, 20, 1861-1865.

DOI: 10.1021/acs.orglett.8b00390 (free Supporting Information)



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Abstract

Trialkylphosphines catalyze a regioselective anti-hydroboration of internal alkynes with pinacolborane reagents to provide (E)-disubstituted alkenylboronate compounds. The alkenylboronates can be used for derivatizations, such as protodeborylations, Suzuki-Miyaura couplings, conjugate reductions, and Diels-Alder reactions.

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Key Words

vinylboronates, organocatalysis


ID: J54-Y2018