Iodine-promoted sequential dual oxidative Csp3–H amination/Csp3–H iodination reactions: efficient synthesis of 1-iodoimidazo[1,5-a]pyridines

doi:10.1039/C6QO00313C

Paper

Iodine-promoted sequential dual oxidative Csp3–H amination/Csp3–H iodination reactions: efficient synthesis of 1-iodoimidazo[1,5-a]pyridines

Published Oct 20, 2016 · Yan‐Dong Wu, Xiao Geng, Qinghe Gao

Organic chemistry frontiers

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19

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Abstract

An iodine-promoted sequential dual oxidative Csp3–H amination of aryl methyl ketones and Csp3–H iodination of pyridin-2-ylmethylamines have been realized for the first time. This simple and efficient approach constructed 1-iodoimidazo[1,5-a]pyridines in moderate to good yields. Based on the preliminary experimental results, a self-sequenced process featuring the iodination/Kornblum oxidation/dual amination/oxidation/iodination mechanism was proposed.

Study Snapshot

This study demonstrates a simple and efficient method for synthesis of 1-iodoimidazo[1,5-a]pyridines using iodine-promoted sequential dual oxidative Csp3-H amination and Csp3-H iodination reactions.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Iodine-promoted sequential dual oxidative Csp3–H amination/Csp3–H iodination reactions: efficient synthesis of 1-iodoimidazo[1,5-a]pyridines

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References

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Iodine-promoted oxidative cross-coupling of anilines and methyl ketones allows for direct C-H bond functionalization, leading to C4-dicarbonylation of anilines in moderate to good yields.

An Efficient Synthesis of Polysubstituted Pyridines via C sp 3H Oxidation and CS Cleavage of Dimethyl Sulfoxide

This study developed an efficient method for preparing substituted pyridines from ketones using a broad substrate scope and ammonium formate as a catalyst, resulting in high yields.

Copper-Catalyzed Denitrogenative Transannulation Reaction of Pyridotriazoles: Synthesis of Imidazo[1,5-a]pyridines with Amines and Amino Acids.

Copper-catalyzed aerobic oxidative synthesis of imidazo[1,5-a]pyridines with benzylamines and amino acids provides a versatile method for obtaining these compounds with good functional group tolerance.

Molecular Iodine-Mediated Chemoselective Synthesis of Multisubstituted Pyridines through Catabolism and Reconstruction Behavior of Natural Amino Acids.

This new process allows for selective construction of multisubstituted pyridines using natural amino acids, with molecular iodine as a catalyst.

Transition metal-catalyzed C–H bond functionalizations by the use of diverse directing groups

Transition metal-catalyzed C-H bond functionalizations using diverse functional groups show high potential for environmentally friendly and efficient construction of C-C and C-hetero bonds.

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