Herein, we describe the intermolecular amination of allyl alcohols with sulfamates, which have been underutilized as nitrogen nucleophiles for allylic amination. Methyl sulfamate is a good nucleophile in the presence of mercuric triflate and efficiently generates monoallylation products in excellent yield at room temperature. Furthermore, the solid‐supported mercuric catalyst silaphenyl mercuric triflate also showed remarkable catalytic activity for the allylic amination.
The hydration of band d-hydroxy internal alkynes catalyzed by Hg(OTf) 2 took place instantaneously to give ketones with complete regioselectivity under mild conditions, whereas the hydration of internal alkyne without hydroxy moiety was very slow and gave a mixture of ketones. If the hydroxy group is located more than five carbons from the triple bond it has no significant effect upon the hydration reaction.
Ketones P 0200Hg (OTf)2-Catalyzed Instantaneous Hydration of βand δ-Hydroxy Internal Alkynes with Complete Regioselectivity. -The reaction time and the kind of product strongly depend on the chain length and substitution pattern of the starting alcohols. -(NISHIZAWA*, M.; TAKEMOTO, T.; SASAKI, I.; NAKANO, M.; HO, E.; NAMBA, K.; YAMAMOTO, H.; IMAGAWA, H.; Synlett 2009, 7, 1175-1179; Fac. Pharm. Sci., Tokushima Bunri Univ., Yamashiro, Tokushima 770, Japan; Eng.) -Lindner 37-048
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.