Concepedia

Selective Reduction of Amides to Amines by Boronic Acid Catalyzed Hydrosilylation

Yuehui Li, Jesús A. Molina de la Torre, Kathleen Grabow, Ursula Bentrup, Kathrin Junge, Shaolin Zhou, Angelika Brückner, Matthias Beller

Angewandte Chemie International Edition · 2013 · 121 citations · 45 references

DOI

Concepts

Abstract

Not a 'B'ore! Benzothiophene-based boronic acids catalyze the reduction of tertiary, secondary, and primary amides in the presence of a hydrosilane. The reaction demonstrates good functional-group tolerance.

References

45

Tris(pentafluorophenyl)boron-Catalyzed Hydrosilation of Aromatic Aldehydes, Ketones, and Esters

Daniel J. Parks, Warren E. Piers · Journal of the American Chemical Society · 1996 · 768 citations

, , +7

Studies on the Mechanism of B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub>-Catalyzed Hydrosilation of Carbonyl Functions

Daniel J. Parks, James M. Blackwell, Warren E. Piers · The Journal of Organic Chemistry · 2000 · 718 citations

, , +13

Zinc-Catalyzed Reduction of Amides: Unprecedented Selectivity and Functional Group Tolerance

Shoubhik Das, Daniele Addis, Shaolin Zhou et al. · Journal of the American Chemical Society · 2010 · 377 citations

, , +14

Selective Reduction of Carboxylic Acid Derivatives by Catalytic Hydrosilylation

Daniele Addis, Shoubhik Das, Kathrin Junge et al. · Angewandte Chemie International Edition · 2011 · 355 citations

, , +13

Controlled and Chemoselective Reduction of Secondary Amides

Guillaume Pelletier, William S. Bechara, André B. Charette · Journal of the American Chemical Society · 2010 · 283 citations

, , +12