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An Efficient Partial Reduction of α,β‐Unsaturated Esters Using DIBAL‐H in Flow
Author(s) -
Yoshida Masahito,
Otaka Hiroyuki,
Doi Takayuki
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402675
Subject(s) - chemistry , benzaldehyde , reduction (mathematics) , redox , hydride , flow (mathematics) , medicinal chemistry , organic chemistry , catalysis , hydrogen , geometry , mathematics
The partial reduction of α,β‐unsaturated esters and benzoate derivatives to form the corresponding aldehydes was achieved using a flow reactor system within 1 s at a high flow rate (18 mL min –1 ) under cryogenic conditions (–97 °C). Commercially available diisobutylaluminium hydride (DIBAL‐H) was used as the reductant. The desired enals and benzaldehyde derivatives, except for 4‐methoxycinnamate and 4‐methoxybenzoate, were formed selectively and redox economically in moderate to high yields.