Multi-functionalization of Rh-carbynoids with alcohols/carbamates and α-propargylic-3-indolymethanols

Herein, we report a multi-functionalization reaction of Rh-carbynoids with alcohols/carbamates and α-propargylic-3-indolymethanols through the trapping of di-heteroatom ylides with carbocations via the S1 pathway. The single carbon atom in Rh-carbynoids was trifunctionalized by three building blocks, leading to the formation of three new bonds in one step and affording a series of propargylic indole derivatives with easily convertible functional groups in moderate to high yields. The key to this reaction is the parallel generation of two activity-matched transient intermediates and the maintenance of high chemo- and regioselectivity.