Anti-Markovnikov stereoselective hydroamination and hydrothiolation of (hetero)aromatic alkynes using a metal-free cyclic trimeric phosphazene base

Add time:08/30/2019    Source:sciencedirect.com

Hydroamination and hydrothiolation are the most efficient and completely atom-economical process to construct important enamine and vinyl sulfide intermediates in pharmaceutical and organic chemistry. The cyclic trimeric phosphazene base (CTPB) showed great catalytic activity for the anti-Markovnikov stereoselective hydroamination and hydrothiolation of alkynes in good to excellent yields. A broad substrate scope of alkynes and nucleophiles was demonstrated, including aryl and heteroaryl alkynes, terminal and internal alkynes, different N-heterocycles, thiols and thiophenols. This versatile and cost-efficient approach with good stereoselectivity and excellent functional group tolerance provided new opportunity for the organocatalyzed hydrofunctionalization of alkynes.

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