A highly regioselective bisselenation of allenes with diphenyl diselenide catalyzed by tetrakis(triphenylphosphine)palladium(0)

Transition metals in organic synthesis: Highlights for the year 2005

“…Rhodium catalyzed the formation of alkynylthioethers from terminal alkynes and disulfides [865]. Palladium catalyzed 1,2-diselenations of allenes using diphenyldiselenide [866] and regioselective hydroselenations of terminal alkynes affording 2-seleno-1-alkenes as the only product [867].…”

Mechanism of methylacetylene bisselenation catalyzed by palladium complex from density functional study

“…12 Similarly, the isocyanide ArNC insertion into PdÀ ÀSe bond 61 and carbon monoxide insertion into PdÀ ÀS bond 62 have been proposed experimentally for bisselenation of isocyanide and azathiolation of carbon monoxide. Furthermore, carbonylative addition of diselenides to allenes has been studied experimentally 43 and theoretically. 48 Thus, it is interesting and necessary to examine the influence of carbon monoxide (CO).…”

“…[1][2][3][4][5][6][7][8][9][10] At the beginning, the group 16 heteroatom compounds were not largely used as reagents in transition-metal-catalyzed reactions, because these compounds had long been considered as catalyst poisons. For example, the addition of SÀ ÀH, [13][14][15][16][17][18][19][20][21][22][23][24] SÀ ÀS, [25][26][27][28][29][30][31][32][33][34][35] SeÀ ÀH, [36][37][38][39][40][41] or SeÀ ÀSe, [27][28][29][30][31][32][33][34][35][42][43]…”

“…11 However, with the finding that palladium (0)-catalyzed disulfide or diselenide addition to carbon-carbon triple bond generated the corresponding functional alkenes with high regio-and stereoselectivities, 12 more and more transition-metal-catalyzed addition reactions of the group 16 heteroatom compounds to the unsaturated organic molecules appeared. For example, the addition of SÀ ÀH, [13][14][15][16][17][18][19][20][21][22][23][24] SÀ ÀS, [25][26][27][28][29][30][31][32][33][34][35] SeÀ ÀH, [36][37][38][39][40][41] or SeÀ ÀSe, [27][28][29][30][31][32][33][34][35][42][43][44] bond to alkynes or allenes has been widely studied to obtain the vinyl or allyl sulfur (or selenyl) compounds.…”

The Formation of Csp 2 S and Csp 2 Se Bonds by Substitution and Addition Reactions Catalyzed by Transition Metal Complexes

“…Ogawa et al have reported allenes bis-selenation with Ph 2 Se 2 and Pd(PPh 3 ) 4 catalyst (Scheme 3.80) [137]. The product was obtained in good to high yields, but with poor stereoselectivity.…”