Lewis acid-promoted conjugate reduction of α,β-unsaturated carbonyl compounds by 2-phenylbenzothiazoline (2-phenyl-2,3-dihydrobenzothiazole)

1987 ◽  
pp. 699-706 ◽  
Author(s):  
Hidenori Chikashita ◽  
Makoto Miyazaki ◽  
Kazuyoshi Itoh
Keyword(s):  
Lewis Acid ◽  
Carbonyl Compounds ◽  
Conjugate Reduction

Ether Synthesis through Reductive Cross-Coupling of Ketones with Alcohols Using Me2SiHCl as both Reductant and Lewis Acid

Synlett ◽  
2017 ◽  
Vol 28 (18) ◽  
pp. 2425-2428 ◽  
Author(s):  
Bill Morandi ◽  
Yong Lee
Keyword(s):  
Functional Groups ◽  
Lewis Acid ◽  
Carbonyl Compounds ◽  
Cross Coupling ◽  
Wide Range ◽  
Direct Cross ◽  
Sterically Hindered ◽  
Polar Functional Groups ◽  
Ether Synthesis ◽  
Dialkyl Ethers

We report that a Lewis acidic silane, Me2SiHCl, can mediate the direct cross-coupling of a wide range of carbonyl compounds with alcohols to form dialkyl ethers. The reaction is operationally simple, tolerates a range of polar functional groups, can be utilized to make sterically hindered ethers, and is extendable to sulfur and nitrogen nucleo­philes.

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