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Palladium Pincer Complex Catalyzed Cross-Coupling of Vinyl Epoxides and Aziridines with Organoboronic Acids

✍ Scribed by Johan Kjellgren; Juhanes Aydin; Olov A. Wallner; Irina V. Saltanova; Kálmán J. Szabó

Publisher
John Wiley and Sons
Year
2005
Tongue
English
Weight
169 KB
Volume
11
Category
Article
ISSN
0947-6539

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✦ Synopsis

Abstract

Palladium‐catalyzed cross‐coupling of vinyl epoxides and aziridines with organoboronic acids was performed by using 0.5–2.5 mol % pincer‐complex catalyst. The reactions proceed under mild conditions affording allyl alcohols and amines with high regioselectivity and in good to excellent yields. Under the applied reaction conditions aromatic chloro‐, bromo‐ and iodo substituents are tolerated. Our results indicate that the mechanism of the pincer complex catalyzed and the corresponding palladium(0) catalyzed process is substantially different. It was concluded that the transformations proceed via transmetalation of the organoboronic acids to the pincer‐complex catalyst followed by an S~N~2′‐type opening of the vinyl epoxide or aziridine substrate. In this process the palladium atom is kept in oxidation state +2 under the entire catalytic process, and therefore oxidative side reactions can be avoided.

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We thank Dr. Pat Carroll of the University of Pennsylvania for X-ray crystallographic analysis. Financial support was provided by Princeton University and kind gifts from Eli Lilly and Sanofi-Aventis. We also thank the MacMillan and Sorensen research groups for use of their chemicals and instruments