Room-Temperature, Copper-Free Sonogashira Reactions Facilitated by Air-Stable, Monoligated Precatalyst [DTBNpP] Pd(crotyl)Cl

Katherine Pohida; David J Maloney; Bryan T Mott; Ganesha Rai

doi:10.1021/acsomega.8b01868

Room-Temperature, Copper-Free Sonogashira Reactions Facilitated by Air-Stable, Monoligated Precatalyst [DTBNpP] Pd(crotyl)Cl

ACS Omega. 2018 Oct 10;3(10):12985-12998. doi: 10.1021/acsomega.8b01868. eCollection 2018 Oct 31.

Authors

Katherine Pohida¹, David J Maloney¹, Bryan T Mott¹, Ganesha Rai¹

Affiliation

¹ National Center for Advancing Translational Sciences, National Institutes of Health, 9800 Medical Center Drive, Rockville, Maryland 20850, United States.

Abstract

A novel application of [DTBNpP] Pd(crotyl)Cl (DTBNpP = di-tert-butylneopentylphosphine) (P2), an air-stable, commercially available palladium precatalyst that allows rapid access to a monoligated state, has been identified for room-temperature, copper-free Sonogashira couplings of challenging aryl bromides and alkynes. The mild reaction conditions with TMP in dimethyl sulfoxide afford up to 97% yields, excellent functional group tolerability, and broad reaction compatibility with access to one-pot indole formation.