7784-68-1Relevant academic research and scientific papers
[Pd(Cl)2(P(NC5H10)(C6H 11)2)2] - A highly effective and extremely versatile palladium-based negishi catalyst that efficiently and reliably operates at low catalyst loadings
Bolliger, Jeanne L.,Frech, Christian M.
experimental part, p. 11072 - 11081 (2010/11/16)
[Pd(Cl)2(P(NC5H10)-(C6H 11)2]2] (1) has been prepared in quantitative yield by reacting commercially available [Pd(cod)(Cl)2] (cod = cyclooctadiene) with readily prepared 1-(dicyclohexylphosphanyl)piperidine in toluene under N2 within a few minutes at room temperature. Complex 1 has proved to be an excellent Negishi catalyst, capable of quantitatively coupling a wide variety of electronically activated, non-activated, deactivated, sterically hindered, heterocyclic, and functionalized aryl bromides with various (also heterocyclic) arylzinc reagents, typically within a few minutes at 100°C in the presence of just 0.01 mol% of catalyst. Aryl bromides containing nitro, nitrile, ether, ester, hydroxy, carbonyl, and carboxyl groups, as well as acetais, lactones, amides, anilines, alkenes, carboxylic acids, acetic acids, and pyridines and pyrimidines, have been successfully used as coupling partners. Furthermore, electronic and steric variations are tolerated in both reaction partners. Experimental observations strongly indicate that a molecular mechanism is operative.
Nickel-catalyzed C-O activation of phenol derivatives with potassium heteroaryltrifluoroborates
Molander, Gary A.,Beaumard, Floriane
supporting information; experimental part, p. 4022 - 4025 (2010/11/05)
A general method based on nickel-catalyzed C-O activation of various phenol derivatives with potassium (hetero)aryltrifluoroborates has been developed. A large number of heterobiaryls can be easily obtained with yields up to 99% using methanesulfonate cross-coupling partners.
Synthesis and characterization of R2PN=P(iBuNCH 2CH2)3N: A new bulky electron-rich phosphine for efficient Pd-assisted Suzuki-Miyaura cross-coupling reactions
Kingston, Jesudoss V.,Verkade, John G.
, p. 2816 - 2822 (2008/02/01)
(Chemical Equation Presented) Pro-azaphosphatrane 1a [P( 1BuNCH2CH2)3N] reacts with iodine under mild conditions to give [IP-(iBuNCH2CH 2)3N]I in excellent yield, which on subsequent reaction with ammonia followed by deprotonation with KOtBu provided HN=P( iBuNCH2CH2)3N (3a) in quantitative yield. Reaction of 3a with R′2PCl afforded sterically bulky electron-rich phosphines of the type R′2PN=P( iBuNCH2CH2)3N (4) [R′ = Ph (4a), iPr (4b), tBu (4c)]. The Pd(OAc)2/4c catalyst system was particularly efficient for the coupling of arylboronic acids with aryl bromides as well as aryl chlorides to give biaryls in excellent yields.
