Regio- and Stereoselective trans-Hydrostannation of Terminal Alkynes Enabled by an Iron Catalyst

Keywords

alkynes - iron catalysis - hydrostannanes - hydrostannation - trans-addition

Significance

Chakrabortty and Fürstner report a highly efficient regio- and stereoselective trans-hydrostannation of terminal alkynes under iron catalysis. The obtained (Z)-alkenyl stannanes are generally made by multistep synthesis and/or by using organometallic reagents that usually limit the functional group tolerance. This protocol is compatible with several functional groups, including free alcohols and amines.

Comment

In the case of unprotected (homo)propargylic alcohols and amines, a directing effect results in the reversed regioselectivity (see gray box). A catalytic cycle according to a modified Chalk–Harrod mechanism is proposed, where initial insertion of the alkyne into the Fe–Sn bond takes place. The observed trans-stereochemistry can be explained by either a transient dipolar carbene or a metallacyclopropene intermediate.

Publication History

Article published online:
26 November 2025