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Cross-Selective Aza-Pinacol Coupling via Atom Transfer Catalysis by Sean M. Rafferty; Joy E. Rutherford; Lumin Zhang; Lu Wang; David A. Nagib is a Chemistry article available to read on EtoBox.

What is Cross-Selective Aza-Pinacol Coupling via Atom Transfer Catalysis about?

A cross-selective aza-pinacol coupling of aldehydes and imines has been developed to afford valuable β-amino alcohols. This strategy enables chemoselective conversion of aliphatic aldehydes to ketyl radicals, in the presence of more easily reduced imines and other functional groups. Upon carbonyl-specific activation by AcI, a photoinitiated Mn catalyst selectively reduces the resulting α-oxy iodide by an atom transfer mechanism. The ensuing ketyl radical selectively couples to imines, precluding homodimerization by a classical reductive approach. In this first example of reductive, ketyl coupling by atom transfer catalysis, Zn serves as a terminal reductant to facilitate Mn catalyst turnover. This new strategy also enables ketyl radical couplings to alkenes, alkynes, aldehydes, propellanes, and chiral imines.

Who reads Cross-Selective Aza-Pinacol Coupling via Atom Transfer Catalysis?

Author

Sean M. Rafferty; Joy E. Rutherford; Lumin Zhang; Lu Wang; David A. Nagib

Publisher

American Chemical Society (ACS)

Published

2021

Language

EN

Field

Chemistry (Physical Sciences)