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In Water and under Mild Conditions: α‐Alkylation of Ketones with Alcohols by Phase‐Transfer‐Assisted Borrowing Hydrogen Catalysis
Author(s) -
Rakers Lena,
Schäfers Felix,
Glorius Frank
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201804308
Subject(s) - alkylation , catalysis , chemistry , alkyl , hydrogen , phase (matter) , organic chemistry , combinatorial chemistry
Abstract Borrowing hydrogen is a powerful and green technique that allows readily available alcohols to be used as alkylating agents and produces water as the only by‐product. Nevertheless, harsh conditions such as high temperatures and organic solvents are usually required. Herein, we present a strategy to perform the α‐alkylation of ketones in aqueous media at mild temperatures by combining borrowing hydrogen with phase‐transfer catalysis. A broad scope of methyl ketones was functionalized with alkyl and benzyl alcohols in moderate to good yields at 40 °C. The protocol was also highly effective at large scale and room temperature.