Unknown

Dataset Information

0

Nondirected, Cu-Catalyzed sp3 C-H Aminations with Hydroxylamine-Based Amination Reagents: Catalytic and Mechanistic Studies.


ABSTRACT: This work demonstrates the use of hydroxylamine-based amination reagents RSO2NH-OAc for the nondirected, Cu-catalyzed amination of benzylic C-H bonds. The amination reagents can be prepared on a gram scale, are benchtop stable, and provide benzylic C-H amination products with up to 86% yield. Mechanistic studies of the established reactivity with toluene as substrate reveal a ligand-promoted, Cu-catalyzed mechanism proceeding through Ph-CH2(NTsOAc) as a major intermediate. Stoichiometric reactivity of Ph-CH2(NTsOAc) to produce Ph-CH2-NHTs suggests a two-cycle, radical pathway for C-H amination, in which the decomposition of the employed diimine ligands plays an important role.

SUBMITTER: Wang A 

PROVIDER: S-EPMC6585460 | biostudies-literature | 2017 Apr

REPOSITORIES: biostudies-literature

altmetric image

Publications

Nondirected, Cu-Catalyzed sp<sup>3</sup> C-H Aminations with Hydroxylamine-Based Amination Reagents: Catalytic and Mechanistic Studies.

Wang Anqi A   Venditto Nicholas J NJ   Darcy Julia W JW   Emmert Marion H MH  

Organometallics 20170323 7


This work demonstrates the use of hydroxylamine-based amination reagents RSO<sub>2</sub>NH-OAc for the nondirected, Cu-catalyzed amination of benzylic C-H bonds. The amination reagents can be prepared on a gram scale, are benchtop stable, and provide benzylic C-H amination products with up to 86% yield. Mechanistic studies of the established reactivity with toluene as substrate reveal a ligand-promoted, Cu-catalyzed mechanism proceeding through Ph-CH<sub>2</sub>(NTsOAc) as a major intermediate.  ...[more]

Similar Datasets

| S-EPMC5831529 | biostudies-literature
| S-EPMC7418105 | biostudies-literature
| S-EPMC6045521 | biostudies-literature
| S-EPMC8640056 | biostudies-literature
| S-EPMC2704946 | biostudies-literature
| S-EPMC10415864 | biostudies-literature
| S-EPMC6020523 | biostudies-literature
| S-EPMC7774803 | biostudies-literature
| S-EPMC7367085 | biostudies-literature
| S-EPMC4416466 | biostudies-literature