Highly E-Selective Synthesis of α-Fluoro-β-arylalkenyl Sulfones from gem-Difluoroalkenes with Sodium Sulfinates

Abstract

The straightforward synthesis of α-fluoro-β-arylalkenyl sulfones under transition-metal- and base-free conditions has been described, which displays broad functional group compatibility and high stereoselectivity. In particular, the strategy is also applied to the late-stage modification of complex natural products and drugs.

Recent Advances in Alkenyl sp2 C–H and C–F Bond Functionalizations: Scope, Mechanism, and Applications

“…813 An efficient approach for the preparation of diverse synthetically valuable α-fluoro-β-arylalkenyl sulfones from gem-difluoroalkenes and sodium sulfinates in the absence of any transition metal or base has been reported by Shi's group (Scheme 521). 814 The protocol demonstrated a wide functional group tolerance with excellent stereoselectivity. Remarkably, this strategy can also be used for late-stage transformation of value-added complex compounds such as drugs and natural products.…”

Copper-catalyzed functionalization/transformation of styrenes with polyhaloalkanes and arenes enables the synthesis of heteroarene-containing gem-dihaloalkenes

“…gem -Dihaloalkenes are a very important class of functional group, which are widely found in bioactive molecules, pesticides and materials. 7 They are also multifunctional frameworks for the construction of C–X (X = P, N and S) bonds 8 and structurally complex molecules, such as alkenes, 9 allenes, 10 alkynes, 11 and various heterocyclic compounds. 12 Classically, numerous methods for the synthesis of gem -dihaloalkenes have been established, 13 the most well-established method being the traditional Wittig-type reaction using carbonyl groups with tetrahalocarbon groups (CX 4 ) in the presence of a stoichiometric amount of PPh 3 .…”

A new method for C(sp2)–H sulfonylmethylation with glyoxylic acid and sodium sulfinates

“…Among them, sodium sulfinates were the most studied. The main approaches to synthesize sulfone derivatives with sodium sulfinates include nucleophilic substitution or addition reactions, 8 oxidative coupling reactions 9 and radical cyclization reactions. 10…”