A General Catalyst for Site-Selective C(sp(3))-H Bond Amination of Activated Secondary over Tertiary Alkyl C(sp(3))-H Bonds.

Autor: Scamp RJ; Department of Chemistry, University of Wisconsin , Madison, Wisconsin 53706, United States., Jirak JG; Department of Chemistry, University of Wisconsin , Madison, Wisconsin 53706, United States., Dolan NS; Department of Chemistry, University of Wisconsin , Madison, Wisconsin 53706, United States., Guzei IA; Department of Chemistry, University of Wisconsin , Madison, Wisconsin 53706, United States., Schomaker JM; Department of Chemistry, University of Wisconsin , Madison, Wisconsin 53706, United States.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2016 Jun 17; Vol. 18 (12), pp. 3014-7. Date of Electronic Publication: 2016 May 26.
DOI: 10.1021/acs.orglett.6b01392
Abstrakt: The discovery of transition metal complexes capable of promoting general, catalyst-controlled and selective carbon-hydrogen (C-H) bond amination of activated secondary C-H bonds over tertiary alkyl C(sp(3))-H bonds is challenging, as substrate control often dominates when reactive nitrene intermediates are involved. In this letter, we report the design of a new silver complex, [(Py5Me2)AgOTf]2, that displays general and good-to-excellent selectivity for nitrene insertion into propargylic, benzylic, and allylic C-H bonds over tertiary alkyl C(sp(3))-H bonds.
Databáze: MEDLINE