American Chemical Society
Browse
cs6b01351_si_001.pdf (1.98 MB)

Ruthenium-NHC Catalyzed α‑Alkylation of Methylene Ketones Provides Branched Products through Borrowing Hydrogen Strategy

Download (1.98 MB)
journal contribution
posted on 2016-05-27, 00:00 authored by Christoph Schlepphorst, Biplab Maji, Frank Glorius
The α-alkylation of a broad range of methylene ketones was achieved using a ruthenium­(II)-NHC catalyst under borrowing hydrogen conditions. Primary alcohols served as alkylating agents and could be used in a one-to-one stoichiometry with respect to the ketone. The selectivity of the process for methyl over branched ketones enabled a one-pot double alkylation protocol utilizing two different alcohols with a single catalyst. Moreover, this methodology could be applied directly to the one-step synthesis of donepezil, the best-selling drug for the treatment of Alzheimer’s disease.

History