A practical route to 2-iodoanilines via the transition-metal-free and base-free decarboxylative iodination of anthranilic acids under oxygen
Literature Information
Publication Date
2021-06-07
DOI
10.1039/D1QO00461A
Impact Factor
5.281
Authors
View Original
Abstract
A simple and practical procedure for synthesizing 2-iodoanilines has been developed. A series of highly regioselective 2-iodoanilines was obtained in satisfactory to good yields (of up to 90%) by carrying out the decarboxylative iodination of readily available anthranilic acids with inexpensive KI and I2 as halogen donors under transition-metal-free and base-free conditions. Oxygen was shown to be necessary for the transformation. This practical decarboxylative iodination route was operationally scalable and shown to exhibit high functional-group tolerance. Control experiments suggested that a radical pathway was involved in the transformation.
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Source Journal
Organic Chemistry Frontiers
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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
Recommended Compounds
![1-Naphthalenesulfonic acid, 2-[(2-hydroxy-1-naphthalenyl)azo]-, bariumsalt (2:1) structure](https://static.chemtradehub.com/structs/110/1103-38-4-0b33.webp "1-Naphthalenesulfonic acid, 2-[(2-hydroxy-1-naphthalenyl)azo]-, bariumsalt (2:1) structure")
1-Naphthalenesulfonic acid, 2-[(2-hydroxy-1-naphthalenyl)azo]-, bariumsalt (2:1)
CAS Number:
1103-38-4
Molecular Formula:
C20H14BaN2O4S
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