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A general method for the one-pot reductive functionalization of secondary amides

Pei-Qiang Huang¹, Ying-Hong Huang, Kai-Jiong Xiao

¹Department of Chemistry and Fujian Provincial Key Laboratory of Chemical Biology, Collaborative Innovation Centre of Chemistry for Energy Materials, College of Chemistry and Chemical Engineering, Xiamen University , Xiamen, Fujian 361005, P. R. China.

The Journal of Organic Chemistry

|February 6, 2015

Summary

This study introduces a new one-pot reaction to convert secondary amides into amines via carbon-carbon bond formation. The versatile method efficiently uses various nucleophiles, even with other functional groups present.

Area of Science:

Organic Chemistry
Synthetic Chemistry

Background:

Secondary amides are common functional groups in organic synthesis.
Efficient methods for amide transformation and C-C bond formation are crucial.

Purpose of the Study:

To develop a novel one-pot reaction for secondary amide conversion to amines.
To achieve C-C bond formation during amide transformation.

Main Methods:

In situ activation of secondary amides using triflic anhydride (Tf2O).
Partial reduction followed by the addition of carbon nucleophiles (hard and soft).
Utilized organometallic reagents (RMgX, RLi) and enolates as nucleophiles.

Main Results:

Successfully transformed secondary amides into amines with concurrent C-C bond formation.
Demonstrated broad scope with both hard and soft nucleophiles.
Achieved high chemoselectivity with soft nucleophiles in the presence of esters, cyano, nitro, and tertiary amides.

Conclusions:

The developed one-pot method offers a versatile and chemoselective route for amide functionalization.
This transformation expands synthetic possibilities for creating complex amine structures.

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