Abstract
A co-catalyst of (PPh3)AuCl/AgOTf for the intermolecular hydroamination of allenes with sulfonamides is shown. The reaction proceeded smoothly under mild conditions for differently substituted allenes giving N-allylic sulfonamides in good yields with high regioselectivity and E-selectivity.
Highlights
Hydroamination of an N–H bond across a C–C unsaturated bond represents one of the most effective and atom-economical methods to prepare amine derivatives [1-5]
As part of our ongoing studies on metal-catalyzed reactions, we have reported the hydroalkoxylation of allenes with alcohols and hydroamination of alkynes with sulfonamides in the presence of gold catalysts [26-28]
We were pleased to find that efficient hydroamination was realized at rt and led to a 91% yield of 3a with good regioselectivity and high E-selectivity (Table 1, entry 6)
Summary
Hydroamination of an N–H bond across a C–C unsaturated bond represents one of the most effective and atom-economical methods to prepare amine derivatives [1-5]. Au(I), Au(III), Pt(II) and Rh(I) have been used for the intermolecular hydroamination of allenes with secondary alkylamines, ammonia, or carboxamide [7,16-24]. Some of these advances have been efficiently made in hydroamination, many require extreme and extended reaction conditions. Development of these reactions is still needed. Yamamoto and co-workers reported the Pd(0)-catalyzed intermolecular hydroamination of allenes with sulfonamides [25]. We wish to develop a gold(I)-complex-catalyzed addition of sulfonamides as the amine partner to allenes to synthesize N-allylic sulfonamides with high regio- and stereoselectivity
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