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Divergent and Stereoselective Synthesis of Tetraarylethylenes from Vinylboronates
Author(s) -
Zhang Minghao,
Yao Yisen,
Stang Peter J.,
Zhao Wanxiang
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202008113
Subject(s) - supramolecular chemistry , stereoselectivity , chemistry , combinatorial chemistry , molecule , aryl , divergent synthesis , nanotechnology , organic chemistry , materials science , catalysis , alkyl
The synthesis of a new tetraborylethylene (TBE) is reported, and its application in the preparation of [4+0]‐tetraarylethenes (TAEs) is elucidated. TAEs have widespread applications in material science and supramolecular chemistry due to their aggregation‐induced emission (AIE) properties. The divergent and stereoselective synthesis of [3+1]‐, [2+2]‐, and [2+1+1]‐TAEs via multiple couplings of vinylboronates with aryl bromides is demonstrated. These couplings feature a broad substrate scope and excellent functional group compatibility due to mild reaction conditions. Facile access to various tetraarylethenes is provided. This strategy represents an important complement to the conventional methods employed for the synthesis of TAEs, and would be a valuable tool for synthesizing TAE‐based molecules useful in functional materials, biological imaging and chemical sensing.