Copper-catalyzed oxidative benzylic C(sp)-H amination: direct synthesis of benzylic carbamates

A new efficient strategy to access benzylic carbamates through C-H activation is reported. The use of a catalytic amount of a Cu( i )/diimine ligand in combination with NFSI ((PhSO 2 ) 2 NF) or F-TEDA-PF 6 as oxidants and H 2 NCO 2 R as an amine source directly leads to the C-N bond formation at the...

Full description

Saved in:
Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2020-10, Vol.56 (85), p.1313-1316
Main Authors: Liu, Shuai, Achou, Raphaël, Boulanger, Coline, Pawar, Govind, Kumar, Nivesh, Lusseau, Jonathan, Robert, Frédéric, Landais, Yannick
Format: Article
Language:English
Subjects:
Carbamates (tradename)
Chemical Sciences
Copper
Organic chemistry
Oxidizing agents
Substrates
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A new efficient strategy to access benzylic carbamates through C-H activation is reported. The use of a catalytic amount of a Cu( i )/diimine ligand in combination with NFSI ((PhSO 2 ) 2 NF) or F-TEDA-PF 6 as oxidants and H 2 NCO 2 R as an amine source directly leads to the C-N bond formation at the benzylic position. The mild reaction conditions and the broad substrate scope make this transformation a useful method for the late-stage incorporation of a ubiquitous carbamate fragment onto hydrocarbons. A Cu( i )-diimine ligand combined with a N-F source allows the C-H abstraction and incorporation of a carbamate functional group in the hydrocarbons at the benzylic position.
ISSN:1359-7345
1364-548X
DOI:10.1039/d0cc05226d