Catalyst- and Stoichiometry-Dependent Deoxygenative Reduction of Esters to Ethers or Alcohols with Borane-Ammonia

被引：11

作者：

Ramachandran, P. Veeraraghavan ^{[1
]}

Alawaed, Abdulkhaliq A. ^{[1
]}

Hamann, Henry J. ^{[1
]}

机构：

[1] Purdue Univ, Dept Chem, W Lafayette, IN 47907 USA

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 37期

关键词：

ORGANIC-COMPOUNDS; NATURAL-PRODUCTS; CONVERSION; STEROIDS;

D O I：

10.1021/acs.orglett.3c02643

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile and selective room temperature deoxygenation of both aromatic and aliphatic carboxylic esters to ethers has been achieved by regulating the stoichiometry of the reductant, BH3-NH3, and the catalyst, TiCl4. This first, practical borane-mediated process is compatible with various potentially sensitive functional groups and is applicable to the deoxygenative ether formation from typically challenging aromatic acid esters. Substituting BF3-Et2O as the catalyst alters the reaction pathway, reducing the esters to alcohols. Mechanistic insights are provided by NMR spectroscopy, deuterium labeling, and kinetic isotope studies.

引用

页码：6902 / 6906

页数：5