Olefin skeletal rearrangement enabling access to multiarylated N-sulfonyl amidines

Chen-Chang Cui, Feng Lin, Lu-Yao Wang, Yin-Ping Liu, Shu-Jiang Tu, Man-Su Tu,* Wen-Juan Hao,* Bo Jiang*

A base-promoted olefin skeletal rearrangement strategy from para-quinone methides (p-QMs) and N-fluoroarenesulfonamides is reported, enabling direct nitrogen insertion of olefins to produce a series of multiarylated (Z)-N-sulfonyl amidines with complete stereoselectivity and generally good yields. Using p-QMs without o-hydroxy substitu-ents gave triarylated N-sulfonyl amidines, whereas tetraarylated N,N’-disulfonyl amidines were synthesized with existence of o-hydroxy groups.

Chem. Commun. 2024, 60, 1492-1495; DOI: 10.1039/D3CC05977D