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Designing Homogeneous Copper-Free Sonogashira Reaction through a Prism of Pd-Pd Transmetalation

Bruno A. Martek, Martin Gazvoda, Damijana Urankar and Janez Košmrlj*

*Faculty of Chemistry and Chemical Technology, University of Ljubljana, Večna pot 113, SI-1000 Ljubljana, Slovenia, Email: janez.kosmrljfkkt.uni-lj.si

B. A. Martek, M. Gazvoda, D. Urankar, J. Košmrlj, Org. Lett., 2020, 22, 4938-4943.

DOI: 10.1021/acs.orglett.0c01227 (free Supporting Information)


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Abstract

The combination of different palladium (pre)catalysts, one tuned to promote oxidative addition to (hetero)aryl bromide and another to activate terminal alkyne substrate, enables a copper-free Sonogashira reaction via a productive Pd-Pd transmetalation. This method is suitable for the synthesis of alkyl, aryl, and heteroaryl substituted alkynes at room temperature.

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Pd-PyMIC


proposed mechanism



Key Words

Sonogashira coupling


ID: J54-Y2020