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Updated: Nov 19, 2025

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Construction of fully substituted carbon centers containing a heteroatom and a CF3 group via in situ generated
Kyu Terashima1, Tomoko Kawasaki-Takasuka1, Takashi Yamazaki1
1Division of Applied Chemistry, Institute of Engineering, Tokyo University of Agriculture and Technology, 2-24-16 Nakamachi, Koganei 184-8588, Japan. tyamazak@cc.tuat.ac.jp.
Abstract:
1,6-Conjugate additions of in situ generated δ-CF3-δ-substituted p-quinone methides have been achieved with a variety of heteronucleophiles under mild conditions, which led to facile and practical construction of fully substituted carbon centers including a heteroatom and a CF3 group. In particular, it was revealed that some amines themselves worked for efficient cleavage of the TBS protective group, and addition of a catalytic amount of an appropriate Brønsted acid was found to sometimes improve the progress of the desired process.
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