Mechanistic switch in dual gold catalysis of diynes: C(sp(3))-H activation through bifurcation--vinylidene versus carbene pathways

Max M Hansmann; Matthias Rudolph; Frank Rominger; A Stephen K Hashmi

doi:10.1002/anie.201208777

Mechanistic switch in dual gold catalysis of diynes: C(sp(3))-H activation through bifurcation--vinylidene versus carbene pathways

Angew Chem Int Ed Engl. 2013 Feb 25;52(9):2593-8. doi: 10.1002/anie.201208777. Epub 2013 Jan 30.

Authors

Max M Hansmann¹, Matthias Rudolph, Frank Rominger, A Stephen K Hashmi

Affiliation

¹ Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany.

PMID: 23362151
DOI: 10.1002/anie.201208777

Abstract

The other side of the mountain: Changing the framework of diyne systems opens up new cyclization modes for dual gold catalysis. Instead of a 5-endo cyclization and gold vinylidenes a 6-endo cyclization gives rise to gold-stabilized carbenes as key intermediates for selective C-H insertions.