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Divergent and Stereoselective Synthesis of Tetraarylethylenes from Vinylboronates
Minghao Zhang1, Yisen Yao1, Peter J Stang2
1State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha, Hunan, 410082, P. R. China.
Abstract:
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.
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