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Issue 19, 2019
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Acceptorless dehydrogenative construction of C[double bond, length as m-dash]N and C[double bond, length as m-dash]C bonds through catalytic aza-Wittig and Wittig reactions in the presence of an air-stable ruthenium pincer complex

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Abstract

The construction of C[double bond, length as m-dash]N bonds was achieved by the dehydrogenative coupling of alcohol and azide via aza-Wittig type reaction. The reaction is catalyzed by an acridine-derived ruthenium pincer complex and does not use any oxidant. The present protocol offers a wide substrate scope, including aliphatic, aryl or heteroaryl alcohol/azides. This expeditious protocol was successfully applied to construct a C[double bond, length as m-dash]C bond directly from alcohol via dehydrogenative Wittig reaction. Furthermore, the synthesis of structurally important pyrrolo[1,4]benzodiazepine derivatives was also achieved by this methodology.

Graphical abstract: Acceptorless dehydrogenative construction of C [[double bond, length as m-dash]] N and C [[double bond, length as m-dash]] C bonds through catalytic aza-Wittig and Wittig reactions in the presence of an air-stable ruthenium pincer complex

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Article information


Submitted
29 Nov 2018
Accepted
03 Apr 2019
First published
03 Apr 2019

Dalton Trans., 2019,48, 6501-6512
Article type
Paper

Acceptorless dehydrogenative construction of C[double bond, length as m-dash]N and C[double bond, length as m-dash]C bonds through catalytic aza-Wittig and Wittig reactions in the presence of an air-stable ruthenium pincer complex

N. Biswas, K. Das, B. Sardar and D. Srimani, Dalton Trans., 2019, 48, 6501
DOI: 10.1039/C8DT04725A

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