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Published on: February 16, 2018
Modular Synthesis of Geminal Triarylmethyl and Chiral Diarylmethyl Boronates via Arylation of Solid α-Boryl
Hao Jin1,2, Shuda Luo1,2, Xin An1,2
1Institute of Medical Research, Northwestern Polytechnical University, Xi'an 710072, China.
Abstract:
Geminal multiarylmethyl moieties are crucial structural components in a wide variety of bioactive and pharmaceutical compounds. Herein, we present a Pd-catalyzed enantioconvergent arylation of racemic stable solid benzylic α-boryl organozinc reagents, enabling the synthesis of chiral gem-diarylmethyl boronates. In addition, the previously unexplored sterically hindered gem-triarylmethyl boronates were readily accessed via successive dual arylation of benzylboronates. The synthetic practicability of gem-triarylmethyl boronates was demonstrated by their conversion to triaryl methanol, triaryl alkane, and tetraarylmethane derivatives.
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