Catalyst-Free 1,6-Conjugate Addition/Aromatization/Sulfonylation of para-Quinone Methides: Facile Access to Diarylmethyl Sulfones

Abstract

An efficient, catalyst-free strategy to construct diarylmethyl sulfones via 1,6-conjugate addition/aromatization/sulfonylation reaction of para -quinone methides with sulfonyl hydrazides under mild and environmentally benign conditions has been developed. The established protocol provided a highly chemo- and regioselectivity synthesis of a diverse array of novel diarylmethyl sulfones with excellent yields, and the reaction could be scaled up.

The crystal structure of 2,6-di-tert-butyl-4-(phenyl(phenylsulfonyl)methyl)phenol, C27H32O3S

“…One month later, Zhu's group deposited another monoclinic crystal structure of the same compound with P21/c space group with the Cambridge Crystallographic Data Center (CCDC no. : 1583037) [14]. There is only one molecule in the asymmetric unit of this monoclinic structure.…”

Oxidative Sulfonylation of Multiple Carbon‐Carbon bonds with Sulfonyl Hydrazides, Sulfinic Acids and their Salts

“…[180] Generation of imine quinone ketals in situ from the corresponding p-methoxy N-substituted anilines by PIDA, followed by sulfonylation with sodium sulfinates, led to 4-methoxy-3-sulfonyl N-substituted anilines in 17-98% yields. [181] The reaction between p-quinone methides 337 and sulfonyl hydrazides 338 [182] or sodium sulfinates 339 [183] resulted in substituted 4-(sulfonylmethyl)phenols 340 in high yields (Scheme 147). Similar products were also prepared by three-component reaction of aldehydes, sodium sulfinates, and di-or trimethoxybenzenes in the presence of Amberlyst-15 in water.…”

“…The reaction between p ‐quinone methides 337 and sulfonyl hydrazides 338 [182] or sodium sulfinates 339 [183] resulted in substituted 4‐(sulfonylmethyl)phenols 340 in high yields (Scheme 147). Similar products were also prepared by three‐component reaction of aldehydes, sodium sulfinates, and di‐ or trimethoxybenzenes in the presence of Amberlyst‐15 in water [184] …”

Recent Advances in the Synthesis of Sulfides, Sulfoxides and Sulfones via C-S Bond Construction from Non-Halide Substrates

“…In the same year, the Liu and Zhu group used the same sulfonylation reagent and found a new method for the synthesis of diaryl methylsulfones via sulfonylation of para-quinone methides (Scheme 51) [73]. The reaction occurred smoothly in the cosolvent of ethanol and water at 50 • C without the use of any catalyst.…”