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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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Publication details

The article was received on 29 Nov 2018, accepted on 03 Apr 2019 and first published on 03 Apr 2019


Article type: Paper
DOI: 10.1039/C8DT04725A
Citation: Dalton Trans., 2019, Advance Article

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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

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

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