4874-72-0Relevant academic research and scientific papers
(t-Bu)2PN=P(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
Reddy, Ch. Venkat,Kingston, Jesudoss V.,Verkade, John G.
, p. 3047 - 3062 (2008/09/19)
(Chemical Equation Presented) By employing Pd(OAc)2, Cs 2CO3, or NaOH, and the new ligand (t-Bu) 2PN=P(i-BuNCH2CH2)3N (3a), an electronically diverse array of aryl bromides and chlorides possessing base-sensitive substituents (nitro, ester, and keto) provide coupling products with bulky aryl amines in good to excellent yields. Aryl halides possessing other functional groups including cyano, amino, trifluoromethyl, and phenol, coupled with equal ease, producing highly functionalized amines in good to excellent yields. Moreover, an aryl chloro group can be preserved in the presence of a bromo substituent under our reaction conditions. BOC-protected amines also participated efficiently. Heterocyclic bromides and chlorides underwent clean couplings with amines in excellent yields. An important strength of our protocol is the use of lower palladium loadings than those reported earlier, without compromising yields. The air-stable palladium complex (η3-cinnamyl)PdCl·(3a) (5) was also employed successfully in C-N coupling reactions while the crotyl analogue was less efficacious. The 3a/Pd(OAc)2 catalyst system promotes, for the first time, efficient coupling of vinyl bromides with a variety of amines to produce imines and enamines at room temperature.
A highly effective catalyst system for the Pd-catalyzed amination of vinyl bromides and chlorides
Reddy, Chinta Reddy Venkat,Urgaonkar, Sameer,Verkade, John G.
, p. 4427 - 4430 (2007/10/03)
(Chemical Equation Presented) A highly efficient synthesis of enamines and imines by Pd-catalyzed amination of vinyl bromides or chlorides with amines is described using the Pd2(dba)3/P(i-BuNCH2CH 2)3N catalyst system.
