Abstract
A straightforward and selective synthesis of 1,2,3,4-tetrahydroquinolines starting from 2-aminobenzyl alcohols and simple secondary alcohols is reported. This one-pot cascade reaction is based on the borrowing hydrogen methodology promoted by a manganese(I) PN3 pincer complex. The reaction selectively leads to 1,2,3,4-tetrahydroquinolines thanks to a targeted choice of base. This strategy provides an atom-efficient pathway with water as the only byproduct. In addition, no further reducing agents are required.
Highlights
Tetrahydroquinolines starting from 2-aminobenzyl alcohols and simple secondary alcohols is reported
While a number of synthetic approaches to tetrahydroquinolines exist,[2] the development of new catalytic processes that provide a faster and more efficient access are highly desirable to reach the goals of a sustainable development.[3]
The borrowing hydrogen (BH) methodology offers a simple opportunity to construct tetrahydroquinolines in an atom- and step-economical manner starting from 2-aminobenzyl alcohols and a second alcohol (Scheme 1, steps a−c) with water as the only byproduct
Summary
Tetrahydroquinolines starting from 2-aminobenzyl alcohols and simple secondary alcohols is reported. Previous attempts in the condensation of 2aminobenzyl alcohols and alcohols have produced only quinolines via an acceptorless dehydrogenative coupling (corresponding to Scheme 1, steps a and b) utilizing precious[9−11] and recently base metal[12−16] catalysts, falling short of completing the whole BH cycle.
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