Air‐Assisted Addition of Grignard Reagents to Olefins. A Simple Protocol for a Three‐Component Coupling Process Yielding Alcohols.

Abstract

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Amino Acid-Catalyzed Direct Synthesis of β-Keto Sulfones via Aerobic Difunctionalization of Terminal Alkynes in an Aqueous Medium

“…37,38 The synthesis of β-keto sulfones involving radical sulfonylation approaches is either through activated alkenes or alkynes. 39,40 In this context, several industrial important processes have been developed, including hydroacylation of α,β-unsaturated esters, 41 Pdcatalyzed Wacker-type oxidation, 42 radical addition of Grignard reagents to olefins, 43 Sonogashira coupling, 44,45 autoxidative coupling reactions, 46,47 and metal-catalyzed reactions 48,49 61 Lipshutz's group also developed the synthesis of β-keto sulfones via an aerobic oxidation in nanomicelles using TPGS-750-M as the surfactant and 2,6-lutidine as the base from aryl alkynes and sulfinic salts, 62 and Yi Li et al reported a two-step synthesis of β-keto sulfones from aryl alkynes and sulfinic salts using rhodium(I) catalyst followed by a visible-light promoted photoredox via vinyl tosylates 63 (Scheme 1). However, all of these methods suffer from drawbacks such as the use of transition-metal catalysts, toxic reagents, and solvents like pyridine/substituted pyridine and chlorinated solvents, an excess amount of base, higher reaction temperature, longer reaction time, and low yield of products.…”