A Diaminochlorophosphine for Palladium‐Catalyzed Arylations of Amines and Ketones

Pd‐Catalyzed Aryl Amination Mediated by Well Defined, N‐Heterocyclic Carbene (NHC)–Pd Precatalysts, PEPPSI

“…The spectral data were in accordance with those reported in literature. [33] 1-(6-Methoxypyridin-2-yl)-4-methylpiperazine (31) ( Table 3): Following general procedure A (RT), the crude residue was taken up in Et 2 O (100 mL) and washed with 1 m HCl (2 50 mL). The organic layer was discarded and the combined aqueous layers were adjusted to pH % 10 using a solution of 10 m KOH.…”

“…[33] 2,4,6-Trimethyl-N-phenylaniline (26) ( Table 3): Following general procedure A (RT), 141 mg of 26 (67 % yield) were isolated (R f = 0.3, 5 % Et 2 O in pentane) as a colorless oil. [33] 2-Piperidinylpyridine (27) ( Table 3): Following general procedure A (RT), 135 mg of 27 (83 % yield) were isolated (R f = 0.3, 10 % Et 2 O in pentane) as a colorless oil. The spectral data were in accordance with those reported in literature.…”

Highly Reactive, General and Long-Lived Catalysts for Palladium-Catalyzed Amination of Heteroaryl and Aryl Chlorides, Bromides, and Iodides: Scope and Structure–Activity Relationships

“…These factors have limited the use of the coupling of amines to produce less expensive intermediates and commodity building blocks. 6,7 (1) Three general classes of reagents react slowly and require high loading of catalyst, even with most of the most recently developed systems: 8 (1) primary alkylamines, [9][10][11][12][13][14][15][16][17][18][19][20][21][22][23] which form substantial amounts of product from diarylation in the absence of an ortho substituent on the haloarene reagent or an excess of the primary amines; (2) heteroaryl halides, 11,12,15,17,19,[24][25][26][27][28][29][30][31][32] which are important for medicinal chemistry applications, but have reacted more slowly, with narrower scope, and with higher catalyst loadings than aryl halides; and (3) aryl iodides, which react more slowly and provide lower yields than aryl bromides in couplings with amine nucleophiles, 15,17,[33][34][35][36][37][38][39][40][41][42]…”

Exploring organic reactions using simple cyclodiphosphazanes

“…(l-N-t-Bu)] 2 (30) as a co-ligand for the palladium catalyzed amination of aryl bromides and chlorides C-N Bond formation by palladium catalyzed cross coupling reaction is one of the powerful techniques in synthetic organic chemistry. To the best of our knowledge, only two reports have appeared describing the utility of chloro(amino)phosphines as ligands in this type of coupling [16]. In this context, we felt that cyclodiphosphazane derivative [ClP(l-N-t-Bu)] 2 (30) bearing a bulky t-butylamino substituent as a ligand should be quite useful.…”