Diisobutylaluminum Hydride Reductions Revitalized: A Fast, Robust, and Selective Continuous Flow System for Aldehyde Synthesis

被引：80

作者：

Webb, Damien ^{[1
]}

Jamison, Timothy F. ^{[1
]}

机构：

[1] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 02期

关键词：

ORGANIC-SYNTHESIS; ESTERS; SCALE; GENERATION; ROUTE;

D O I：

10.1021/ol2031872

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A continuous flow system for the multiparameter (flow rate, temperature, residence time, stoichiometry) optimization of the DIBALH reduction of esters to aldehydes is described. Incorporating an in-line quench (MeOH), these transformations are generally complete in fewer than 60 s. Mixing of the DIBALH and ester solutions was observed to be an exceptionally critical parameter for optimum results. This system thus provides general guidelines based on the structure of the ester for selective reduction of an ester without overreduction.

引用

页码：568 / 571

页数：4

共 35 条

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