Rhodium-Catalyzed Annulation of Phenacyl Ammonium Salts with Propargylic Alcohols via a Sequential Dual C–H and a C–C Bond Activation: Modular Entry to Diverse Isochromenones

Reddy Singam, Maneesh Kumar; Suri Babu, Undamatla; Suresh, Vavilapalli; Nanubolu, Jagadeesh Babu; Sridhar Reddy, Maddi

Rhodium-Catalyzed Annulation of Phenacyl Ammonium Salts with Propargylic Alcohols via a Sequential Dual C–H and a C–C Bond Activation: Modular Entry to Diverse Isochromenones

2021

Reddy Singam, Maneesh Kumar | Suri Babu, Undamatla | Suresh, Vavilapalli | Nanubolu, Jagadeesh Babu | Sridhar Reddy, Maddi

Given their omnipresence in natural products and pharmaceuticals, isochromenone congeners are one of the most privileged scaffolds to synthetic chemists. Disclosed herein is a dual (ortho/meta) C–H and C–C activation of phenacyl ammonium salts (acylammonium as traceless directing group) toward annulation with propargylic alcohols to accomplish rapid access for novel isochromenones by means of rhodium catalysis from readily available starting materials. This operationally simple protocol features broad substrate scope and wide functional group tolerance. Importantly, the protocol circumvents the need of any stoichiometric metal oxidants and proceeds under aerobic conditions.

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