Abstract
A highly efficient sulfonylation of para-quinone methides with sulfonyl hydrazines in water has been developed on the basis of the mode involving a tetrabutyl ammonium bromide (TBAB)-promoted sulfa-1,6-conjugated addition pathway. This reaction provides a green and sustainable method to synthesize various unsymmetrical diarylmethyl sulfones, showing good functional group tolerance, scalability, and regioselectivity. Further transformation of the resulting diarylmethyl sulfones provides an efficient route to some functionalized molecules.
Highlights
IntroductionAs aa class class of of sulfur-containing sulfur-containing compounds, compounds, sulfones sulfones are are widely widely used used in in organic organic synthesis, synthesis, pharmaceuticals, agrochemicals, and materials science [1,2,3,4,5,6,7]
AsAs aa class class of of sulfur-containing sulfur-containing compounds, compounds, sulfones sulfones are are widely widely used used in in organic organic synthesis, synthesis, pharmaceuticals, agrochemicals, and materials science [1,2,3,4,5,6,7].Among the sulfone family, pharmaceuticals, agrochemicals, and materials science [1,2,3,4,5,6,7]
A number of methodologies have been developed for the synthesis of diarylmethyl sulfones, most of the reported methods suffer from the harsh reaction conditions, multi-step procedures, Molecules 2020, 25, x; doi: FOR PEER REVIEW
Summary
As aa class class of of sulfur-containing sulfur-containing compounds, compounds, sulfones sulfones are are widely widely used used in in organic organic synthesis, synthesis, pharmaceuticals, agrochemicals, and materials science [1,2,3,4,5,6,7]. A number of methodologies have been developed for the synthesis of diarylmethyl sulfones, most of the reported methods suffer from the harsh reaction conditions, multi-step procedures, Molecules 2020, 25, x; doi: FOR PEER REVIEW www.mdpi.com/journal/molecules. With our keen interest in the sulfa-1,6-conjugated addition reactionwe [15,39,40], we try the to green and sustainable chemical synthetic concept and the. Combine the green and sustainable chemical synthetic concept and the C-S bonding formation we discloseHerein, a highly ammonium bromide (TBAB)-promoted sulfonylation of reactions. With sulfonyl hydrazines to afford unsymmetrical gem-diarylmethyl sulfonylation of para-quinone methide (p-QM) with sulfonyl hydrazines to afford unsymmetrical sulfones via a sulfa-1,6-conjugated addition pathway. Synthesis of unsymmetrical gem-diarylmethyl sulfones via sulfa-1,6-conjugated inaddition water. Synthesis of unsymmetrical gem-diarylmethyl sulfones via sulfa-1,6-conjugated inaddition water. in water
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