Deprotonative Generation and Trapping of Haloaryllithium in a Batch Reactor
Yuxuan Feng, Taro Yukioka, Mei Matsuyama, Atsunori Mori and Kentaro Okano*
*Department of Chemical Science and Engineering, Kobe University, 1-1 Rokkodai, Nada,
Kobe 657-8501, Japan, Email: okano
harbor.kobe-u.ac.jp
Y. Feng, T. Yukioka, M. Matsuyama, A. Mori, K. Okano, Org. Lett., 2023, 25, 3013-3017.
DOI: 10.1021/acs.orglett.3c00800
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Abstract
A method for the regioselective functionalization of haloarenes through deprotonative lithiation, followed by trapping with a zinc chloride diamine complex provides organozinc species without aryne formation. A subsequent reaction with electrophiles affords the corresponding products in good yields. This method was applied to the five-step total synthesis of carbazomycin A.
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Key Words
iodination, directed ortho metalation
ID: J54-Y2023
