A novel palladium(0)-catalyzed addition of diphenyl disulfide to allenes leading to vicinal disulfides and its application to carbonylation with carbon monoxide

Organometallic Approaches to Carbon–Sulfur Bond Formation

“…This process is thought to involve H 2 O and PPh 3 -mediated reduction of the disulfide to the corresponding thiol. In support of this hypothesis, dithiolation is obtained in the absence of H 2 O (26) [183]. In the presence of CO, thiocarbonylation occurs (27) [183].…”

“…In support of this hypothesis, dithiolation is obtained in the absence of H 2 O (26) [183]. In the presence of CO, thiocarbonylation occurs (27) [183]. Further advances are expected to improve the selectivity of this process.…”

“…A wide variety of sulfur derivatives can be used in these processes producing an array of interesting synthetic intermediates. These organosulfur compounds can be: free thiol [164, 167-170, 175, 190, 193, 197, 202, 204], disulfide [160,165,183,207], thiocyanate [179,182,186], thioborate [161], thiostannane [196], sulfenamide [180], and thioester [187,189,191,194,195]. Palladium catalyzed thiocarbonylation, and the development of multicomponent reactions centering on hydrothiolation with free thiols and disulfides has been reviewed extensively [19, 20, 23-26, 167, 227-231].…”

“…Pd(PPh 3 ) 4 allene hydrothiolation carbonylation sequence [183] In 2006, Krause and Nakamura independently reported the first examples of Aucatalyzed transformations of sulfur-containing reagents [11,247]. These reports are particularly notable, as they dispel the myth of sulfur-gold incompatibility.…”

Palladium-catalyzed approach to the synthesis of five-membered O-heterocycles

“…Palladium catalyzed carbonylative transformations involving allenes [41][42][43][44][45][46] and halides [47] are a useful tool for the preparation of several heterocycles and aromatic carbonyl compounds. However, much less attention has been paid to three-component reactions involving N-or O-substituted allenes, carbon monoxide and aromatic halides (Scheme 11) [48].…”