Organic Chemistry Portal

Abstracts

Search:

Palladium-Catalyzed Carbonylative Sonogashira Coupling of Aryl Bromides Using Near Stoichiometric Carbon Monoxide

Karoline T. Neumann, Simon R. Laursen, Anders T. Lindhardt*, Benny Bang-Andersen and Troels Skrydstrup*

*Aarhus University, Finlandsgade 22, 8200 Aarhus N, Denmark; Aarhus University, Gustav Wieds Vej 14, 8000 Aarhus C, Denmark, Email: lindhardteng.au.dk, tschem.au.dk

K. T. Neumann, S. R. Laursen, A. T. Lindhardt, B. Bang-Andersen, T. Skrydstrup, Org. Lett., 2014, 16, 2216-2219.

DOI: 10.1021/ol5007289 (free Supporting Information)



see article for more reactions

Abstract

A palladium-catalyzed carbonylative Sonogashira coupling of aryl bromides using near stoichiometric amounts of carbon monoxide converts a broad substrate scope in good yields. The formed alkynone motive serves as a platform for the synthesis of various heterocyclic structures, including pyrimidines. Furthermore, the presented strategy allows effective 13C labeling.

see article for more examples



Palladium Catalyzed Carbonylative Heck Reaction Affording Monoprotected 1,3-Ketoaldehydes

T. M. Gøgsig, D. U. Nielsen, A. T. Lindhardt, T. Skrydstrup, Org. Lett., 2012, 14, 2536-2539.


Key Words

Sonogashira coupling, Aryl Ketones, Alkynyl Ketones


ID: J54-Y2014