Platinum-Catalyzed Acrylonitrile Hydrophosphination via Olefin Insertion into a Pt−P Bond

Electrophilic Activation of Alkenes by Platinum(II): So Much More Than a Slow Version of Palladium(II)

“…(26)]. [97,98] Phosphines were shown to Originally, a mechanism analogous to Scheme 3 was proposed, in which the initial PÀH oxidative addition to Pt 0 is followed by a regioselective alkene insertion into the PtÀP bond, and subsequent CÀH reductive elimination releases the product to complete the catalytic cycle.…”

Microwave-assisted solventless single and double addition of HP(O)Ph2 to alkynes

“…Glueck and Pringle investigated the platinum-catalyzed addition of H-PR 2 to activated alkenes such as acrylonitrile [4,5], and Tanaka and co-workers reported the rhodiumcatalyzed addition of HP(O)Ph 2 to alkynes [6] as well as the hydrophosphorylation of alkenes using a pinacol-derived hydrogen phosphonate [7]. Recently, Deprele and Montchamp have reported the addition of H 2 P(O)OR to alkenes [8].…”

The Mechanism for Transition-Metal-Catalyzed Hydrochalcogenation of Unsaturated Organic Molecules

“…The activity decreases compared with the case of hydroxyalkynes, which is explained in terms of the larger enthalpic barrier in the turnover-limiting process of the intramolecular insertion step [42]. A theoretical study by Tobisch [43] supports this mechanism and showed that reactive La(OR) 3 [45]. The reaction of 1-octyne with PhSH and CO in the presence of 3 mol% of 30 gave the hydrothiocarboxylation product 31 in 77% yield (19 (38) at 80 C. Thus, a catalytic cycle shown in Scheme 18 was proposed [46].…”

“…In relation, Pringle and coworkers reported the reaction of PH 3 with acrylonitrile catalyzed by Pt[P(CH 2 CH 2 CN) 3 ] 3 to yield P(CH 2 CH 2 CN) 3 [47]. They proposed that the reaction proceeds through oxidative addition of the P-H followed by insertion of acrylonitrile into the Pt-P bond (not Pt-H) bond and a C-H reductive elimination (Scheme 19) [45].…”