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. 2018 Sep 26;140(38):11931-11934.
doi: 10.1021/jacs.8b08385. Epub 2018 Sep 17.

Acceptorless Dehydrogenative Coupling Using Ammonia: Direct Synthesis of N-Heteroaromatics from Diols Catalyzed by Ruthenium

Prosenjit Daw  1 , Yehoshoa Ben-David  1 , David Milstein  1
Affiliations

Acceptorless Dehydrogenative Coupling Using Ammonia: Direct Synthesis of N-Heteroaromatics from Diols Catalyzed by Ruthenium

Prosenjit Daw et al. J Am Chem Soc. .

Abstract

The synthesis of N-heteroaromatic compounds via an acceptorless dehydrogenative coupling process involving direct use of ammonia as the nitrogen source was explored. We report the synthesis of pyrazine derivatives from 1,2-diols and the synthesis of N-substituted pyrroles by a multicomponent dehydrogenative coupling of 1,4-diols and primary alcohols with ammonia. The acridine-based Ru-pincer complex 1 is an effective catalyst for these transformations, in which the acridine backbone is converted to an anionic dearomatized PNP-pincer ligand framework.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Scheme 1
Scheme 1. Synthesis of Pyrazines and Pyrroles from Alcohols and Ammonia Catalyzed by a Ruthenium Complex
Scheme 2
Scheme 2. Synthesis of Complex 3 and a Catalytic Experiment with Catalyst 2
Scheme 3
Scheme 3. Proposed Mechanism
See this image and copyright information in PMC

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