Divergent and Stereoselective Synthesis of Tetraarylethylenes from Vinylboronates

Minghao Zhang; Yisen Yao; Peter J Stang; Wanxiang Zhao

doi:10.1002/anie.202008113

Divergent and Stereoselective Synthesis of Tetraarylethylenes from Vinylboronates

Angew Chem Int Ed Engl. 2020 Nov 2;59(45):20090-20098. doi: 10.1002/anie.202008113. Epub 2020 Aug 31.

Authors

Minghao Zhang¹, Yisen Yao¹, Peter J Stang², Wanxiang Zhao¹

Affiliations

¹ State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha, Hunan, 410082, P. R. China.
² Department of Chemistry, University of Utah, 315 South 1400 East, Room 2020, Salt Lake City, UT, 84112, USA.

PMID: 32696545
DOI: 10.1002/anie.202008113

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.

Keywords: aggregation-induced emission; boron; fluorophores; tetraarylethylenes; vinylboronates.

Publication types

Research Support, Non-U.S. Gov't