Diversity-oriented synthesis of stereodefined tetrasubstituted alkenes via a modular alkyne gem-addition strategy

Xuan Di, Sitian Zhou, Yali Qin, Wenjun Li, Yue Zhang, Jie Zhang, Xu Shen, Jie Han (), Jin Xie () and Hongming Jin ()
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Xuan Di: Nanjing University of Chinese Medicine
Sitian Zhou: Nanjing University
Yali Qin: Nanjing University of Chinese Medicine
Wenjun Li: Nanjing University of Chinese Medicine
Yue Zhang: Nanjing University of Chinese Medicine
Jie Zhang: Nanjing University of Chinese Medicine
Xu Shen: Nanjing University of Chinese Medicine
Jie Han: Nanjing University
Jin Xie: Nanjing University
Hongming Jin: Nanjing University of Chinese Medicine

Nature Communications, 2025, vol. 16, issue 1, 1-12

Abstract: Abstract Stereocontrolled construction of tetrasubstituted olefins has been an attractive issue yet remains challenging for synthetic chemists. In this manuscript, alkynyl selenides, when treated with ArBCl2, are subject to an exclusive 1,1-carboboration, affording tetrasubstituted alkenes with excellent levels of E-selectivity. Detailed mechanistic studies, supported by DFT calculations, elucidates the role of selenium in this 1,1-addition process. Coupled with subsequent C-B and C-Se bond transformations, this 1,1-addition protocol constitutes a modular access to stereodefined all-carbon tetrasubstituted alkenes. The merit of this approach is demonstrated by programmed assembly of diverse functionalized multi-arylated alkenes, especially enabling the stereospecific synthesis of all six possible stereoisomers of tetraarylethene (TAE) derived from the random permutation of four distinct aryl substituents around the double bond. The diversity-oriented synthesis is further utilized to explore different TAE luminogenic properties and potential Se-containing antitumor lead compounds.

Date: 2025
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DOI: 10.1038/s41467-025-56184-3

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