Manganese‐Catalyzed Hydrogen‐Autotransfer C−C Bond Formation: α‐Alkylation of Ketones with Primary Alcohols

Miguel Peña‐López, Patrick Piehl, Saravanakumar Elangovan, Helfried Neumann, Matthias Beller

Angewandte Chemie International Edition · 2016 · 331 citations · 57 references

Concepts

Abstract

A novel catalytic hydrogen-autotransfer protocol for the atom-efficient α-alkylation of ketones with readily available alcohols is presented. The use of manganese complexes bearing non-innocent PNP pincer ligands enabled the functionalization of a broad range of valuable ketones, including 2-oxindole, estrone 3-methyl ether, and testosterone. Mechanistic investigations suggest the participation of an intramolecular amidate-assisted alcohol-dehydrogenation process.

References

57