Bismuth Trichloride Catalyzed Efficient Reductive Etherification of Carbonyl Compounds with Alcohols: A Novel Method for Preparation of Symmetrical and Unsymmetrical Ethers

Abstract

The reductive homocoupling of a carbonyl compound and heterocoupling of a carbonyl compound with a non-protected alcohol were both effected smoothly at room temperature with triethylsilane in the presence of a catalytic amount of bismuth trichloride to afford the corresponding ethers in good yields.

Thiazolium‐Based Catalysts for the Etherification of Benzylic Alcohols under Solvent‐Free Conditions

“…Moreover, they can find application in gasoline and diesel blends. Reductive etherification from carbonyl compounds can be achieved using organosilanes and Lewis acid catalysts such as BiCl 3 [12] or FeCl 3 . [5][6][7] An alternative methodology is represented by the use of Lewis acid catalysts.…”

Bi(OTf)3-, TfOH-, and TMSOTf-Mediated, One-Pot Epoxide Rearrangement, Addition, and Intramolecular Silyl-Modified Sakurai (ISMS) Cascade toward Dihydropyrans: Comparison of Catalysts and Role of Bi(OTf)3

“…1 Catalytic quantities of Bi(III) compounds are effective in promoting allylations and cyanations, 2 etherification, 3 Diels-Alder, 4 and protection/deprotection reactions. Furthermore, asymmetric total syntheses of leucascandrolide, 5 centrolobine, 6 mucocin 7 and bistramide C 8 have included Bi(III)-mediated sequences.…”

A Concise Synthesis of a Very Late Antigen-4 Antagonist <i>trans</i>-4-[1-[[2,5-Dichloro-4-(1-methyl-3-indolylcarboxyamide)phenyl]acetyl]-(4<i>S</i>)-methoxy-(2<i>S</i>)-pyrrolidinylmethoxy]cyclohexanecarboxylic Acid <i>via</i> Reductive Etherification

“…Reductive etherification [6][7][8][9][10][11][12][13][14][15][16] of silyl ethers with carbonyl compounds using triethylsilane as a reductive agent and Lewis acids such as trimethylsilyl trifluoromethanesulfonate (TMSOTf), 6,7) trimethyl iodosilane (TMSI), 8,9) TrClO 4 , 10) BiBr 3 , 11) BiCl 3 , 12) CuOTf, 13) InCl 3 , 14) FeCl 3 15,16) as a catalyst, is a useful transformation reaction in organic synthesis. It is well known that the etherification works well even in case of a secondary alkoxy silyl ethers with ketone in Chart 2.…”