Electroselective C(sp3)–H deuteration of isoindolinones
Literature Information
Publication Date
2023-11-10
DOI
10.1039/D3QO01782F
Impact Factor
5.281
Authors
Qiansong Gao, Lianyou Zheng, Shulin Ning, Lingling Shi, Cheng Wu, Mian Liu, Jinbao Xiang
View Original
Abstract
Development of precise deuteration reactions is highly desirable for organic synthesis, analytical chemistry and pharmaceutical chemistry. The electrochemical C(sp3)–H deuteration of isoindolinones via a H/D exchange reaction is presented for the first time. This paired electrochemical protocol provides an efficient way to synthesize deuterated isoindolinones under mild neutral conditions (39 examples, up to 97% D-incorporation). This precise deuteration method can be used for site-selective D-labeling of a number of pharmaceutical molecules. Furthermore, valuable bisdeuterated isoindolines are generally accessible via a reduction of isoindolinones. This protocol provides an efficient route for the construction of C–D bonds with high regioselectivity.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
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N-{[(2-Methyl-2-propanyl)oxy]carbonyl}-L-methionylglycine
CAS Number:
23446-03-9
Molecular Formula:
C12H22N2O5S
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CAS Number:
2101206-92-0
Molecular Formula:
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CAS Number:
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Molecular Formula:
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