We report the palladium-catalyzed, dearomative syn-1,2- diamination of the non-activated arenes benzene and naphthalene using aryl isocyanates. This reaction proceeds with exclusive syn-1,2-selectivity and provides a complementary regio- and stereoselectivity to previously described arenophile-based transformations. The products are amenable to further synthetic elaboration, including selective diene functionalization and heterocycle cleavage. Overall, this dearomatization provides synthetic access to unprecedented saturated nitrogencontaining heterocyclic motifs and syn-1,2-diaminated cyclohexane products.
Dearomative syn -1,2-Diamination of Benzene and Naphthalene
Bingham T. W.;Sarlah D.
2021-01-01
Abstract
We report the palladium-catalyzed, dearomative syn-1,2- diamination of the non-activated arenes benzene and naphthalene using aryl isocyanates. This reaction proceeds with exclusive syn-1,2-selectivity and provides a complementary regio- and stereoselectivity to previously described arenophile-based transformations. The products are amenable to further synthetic elaboration, including selective diene functionalization and heterocycle cleavage. Overall, this dearomatization provides synthetic access to unprecedented saturated nitrogencontaining heterocyclic motifs and syn-1,2-diaminated cyclohexane products.File in questo prodotto:
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