Regioselective Arene C-H Alkylation Enabled by Organic Photoredox Catalysis.
Angew Chem Int Ed Engl
; 59(19): 7425-7429, 2020 05 04.
Article
in En
| MEDLINE
| ID: mdl-32068943
ABSTRACT
Expanding the toolbox of C-H functionalization reactions applicable to the late-stage modification of complex molecules is of interest in medicinal chemistry, wherein the preparation of structural variants of known pharmacophores is a key strategy for drug development. One manifold for the functionalization of aromatic molecules utilizes diazo compounds and a transition-metal catalyst to generate a metallocarbene species, which is capable of direct insertion into an aromatic C-H bond. However, these high-energy intermediates can often require directing groups or a large excess of substrate to achieve efficient and selective reactivity. Herein, we report that arene cation radicals generated by organic photoredox catalysis engage in formal C-H functionalization reactions with diazoacetate derivatives, furnishing sp2 -sp3 coupled products with moderate-to-good regioselectivity. In contrast to previous methods utilizing metallocarbene intermediates, this transformation does not proceed via a carbene intermediate, nor does it require the presence of a transition-metal catalyst.
Key words
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Photochemistry
/
Alkylation
Language:
En
Journal:
Angew Chem Int Ed Engl
Year:
2020
Document type:
Article
Affiliation country:
United States