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Palladium Pincer Complex Catalyzed Cross‐Coupling of Vinyl Epoxides and Aziridines with Organoboronic Acids
Author(s) -
Kjellgren Johan,
Aydin Juhanes,
Wallner Olov A.,
Saltanova Irina V.,
Szabó Kálmán J.
Publication year - 2005
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200500270
Subject(s) - pincer movement , palladium , chemistry , catalysis , regioselectivity , transmetalation , aziridine , organic chemistry , epoxide , combinatorial chemistry , ring (chemistry)
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.