Transition Metal‐Free Difunctionalization of C−C Bond with Sodium Sulfinates and Water Leading to (E)‐1‐Phenyl‐4‐sulfonylbut‐1‐enes

Abstract

Without using any transitionmetal and base, an eco-friendly, practical and economical protocol has been established for the one-pot synthesis of diverse (E)-1-phenyl-4-sulfonylbut-1-enes from easily accessible starting materials. This strategy features a wide substrate scope, tolerates a broad range of functional groups, employs a less expensive oxidant, is operationally simple, and can be easily scaled-up.

Synthesis and applications of sodium sulfinates (RSO2Na): a powerful building block for the synthesis of organosulfur compounds

“…The Tang group successfully established that the difunctionalization of C–C σ-bonds in a variety of aryl-substituted methylenecyclopropanes was carried out with sodium trifluoromethanesulfinate to generate a series of corresponding functionalized ( E )-4-sulfonylbut-1-enes in moderate to good yields ( Scheme 270 ). 378 Based on the outcome, the electronic and steric effects had almost no influence on the transformation. Although wide ranges of arylsulfinates also readily participated, however, 2-thiophenyl sulfinate and aliphatic sulfinates did not afford the desired products.…”

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

“…During the process, cyclopropane ring is opened leading to 1substituted-4-sulfonyl but-1-enes 40 in high yields (Scheme 22). [30] Formal anti-Markovnikov sulfonylation of double bonds with the assistance of oxime group was carried out photochemically with sulfonyl hydrazides 42 as sulfonyl sources. In this synthesis, addition process takes place (Scheme 23).…”

“…During the process, cyclopropane ring is opened leading to 1‐substituted‐4‐sulfonyl but‐1‐enes 40 in high yields (Scheme 22). [30] …”