Distal p -benzylic deuteration via N-heterocyclic carbene catalyzed ring opening of p -cyclopropylbenzaldehydes

Deuterium incorporation at selective sites of organic compounds has long attracted the interest of the pharmaceutical industry. Here, we present a distal -benzylic deuteration N-heterocyclic carbene catalyzed ring-opening of cyclopropylbenzaldehydes with MeOD as the deuterium source. The correspondi...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2023-06, Vol.21 (23), p.4750-4754
Main Authors: Qiu, Ye, Dai, Lei, Gao, Zhong-Hua, Ye, Song
Format: Article
Language:English
Subjects:
Carbenes
Deuteration
Deuterium
Organic compounds
Pharmaceutical industry
Ring opening
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Summary:Deuterium incorporation at selective sites of organic compounds has long attracted the interest of the pharmaceutical industry. Here, we present a distal -benzylic deuteration N-heterocyclic carbene catalyzed ring-opening of cyclopropylbenzaldehydes with MeOD as the deuterium source. The corresponding 4-alkylbenzoates with high deuterium incorporation at the benzylic position were obtained in good yields. The stable benzylic deuterium remained intact for further chemical transformations.
ISSN:1477-0520
1477-0539
DOI:10.1039/d3ob00394a