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(t-Bu)2PNP(i-BuNCH2CH2)3N: New Efficient Ligand for Palladium-Catalyzed C-N Couplings of Aryl and Heteroaryl Bromides and Chlorides and for Vinyl Bromides at Room Temperature

Ch. Venkat Reddy, Jesudoss V. Kingston and John G. Verkade*

*Department of Chemistry, Iowa State University, Ames, Iowa 50011, Email: jverkadeiastate.edu

Ch. V. Reddy, J. V. Kingston, J. G. Verkade, J. Org. Chem., 2008, 73, 3047-3062.

DOI: 10.1021/jo702367k (free Supporting Information)


Abstract

By employing Pd(OAc)2 and (t-Bu)2PNP(i-BuNCH2CH2)3N as ligand, a broad range of aryl bromides and chlorides possessing base-sensitive substituents provide coupling products with bulky aryl amines in good to excellent yields. An efficient coupling of vinyl bromides with a variety of amines produces imines and enamines at room temperature.


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P(i-BuNCH2CH2)3N: An Effective Ligand in the Palladium-Catalyzed Amination of Aryl Bromides and Iodides

S. Urgaonkar, M. Nagarajan, J. G. Verkade, J. Org. Chem., 2003, 68, 452-459.


Key Words

Buchwald-Hartwig Coupling, Arylamines, Imines, Enamines


ID: J42-Y2008-1060