Highly Regioselective Palladium-catalyzed Double Hydroselenation of Terminal Alkynes with Benzeneselenol in the Presence of Acetic Acid

Abstract

Palladium diacetate (Pd(OAc)2), in the presence of acetic acid, is found to exhibit excellent catalytic activity for the double hydroselenation of terminal alkynes with benzeneselenol to yield the corresponding diselenoketals regioselectively.

Mn-, Fe-, and Co-Catalyzed Radical Hydrofunctionalizations of Olefins

“…This is commonly attributed to catalyst poisoning via metal binding, or to formation of aggregates. 356 …”

“…While there are numerous examples in the literature of transition-metal-catalyzed addition of heteroatom compounds to alkynes, alkenes, and allenes, these transformations tend to proceed rather inefficiently when sulfur or selenium atoms are involved. This is commonly attributed to catalyst poisoning via metal binding, or to formation of aggregates …”

“…This is commonly attributed to catalyst poisoning via metal binding, or to formation of aggregates. 356 In 1990 Kano and co-workers reported the hydrothiolation of styrenes using a porphinatoiron(III) catalyst with diphenyl disulfide and sodium borohydride (Figure 129). 357 The reaction led to the desired product 282 in moderate yield after 24 h at room temperature in a 1:1 mixture of benzene and ethanol.…”