Synthesis of Pyrazines and Quinoxalines via Acceptorless Dehydrogenative Coupling Routes Catalyzed by Manganese Pincer Complexes

Prosenjit Daw; Amit Kumar; Noel Angel Espinosa-Jalapa; Yael Diskin-Posner; Yehoshoa Ben-David; David Milstein

doi:10.1021/acscatal.8b02208

Synthesis of Pyrazines and Quinoxalines via Acceptorless Dehydrogenative Coupling Routes Catalyzed by Manganese Pincer Complexes

Prosenjit Daw, Amit Kumar, Noel Angel Espinosa-Jalapa, Yael Diskin-Posner, Yehoshoa Ben-David, David Milstein

Weizmann Institute of Science, Israel

Research output: Contribution to journal › Article › peer-review

50 Citations (Scopus)

Abstract

Base-metal catalyzed dehydrogenative self-coupling of 2-amino alcohols to selectively form functionalized 2,5-substituted pyrazine derivatives is presented. Also, 2-substituted quinoxaline derivatives are synthesized by dehydrogenative coupling of 1,2-diaminobenzene and 1,2-diols. In both cases, water and hydrogen gas are formed as the sole byproducts. The reactions are catalyzed by acridine-based pincer complexes of earth-abundant manganese.

Original language	English
Pages (from-to)	7734-7741
Number of pages	8
Journal	ACS Catalysis
Volume	8
Issue number	9
DOIs	https://doi.org/10.1021/acscatal.8b02208
Publication status	Published - Sep 7 2018

Keywords

dehydrogenative coupling
manganese
pincer
pyrazine
quinoxaline

ASJC Scopus subject areas

Catalysis
Chemistry(all)

Access to Document

10.1021/acscatal.8b02208

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Synthesis of Pyrazines and Quinoxalines via Acceptorless Dehydrogenative Coupling Routes Catalyzed by Manganese Pincer Complexes. / Daw, Prosenjit; Kumar, Amit; Espinosa-Jalapa, Noel Angel; Diskin-Posner, Yael; Ben-David, Yehoshoa; Milstein, David.

In: ACS Catalysis, Vol. 8, No. 9, 07.09.2018, p. 7734-7741.

Research output: Contribution to journal › Article › peer-review

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abstract = "Base-metal catalyzed dehydrogenative self-coupling of 2-amino alcohols to selectively form functionalized 2,5-substituted pyrazine derivatives is presented. Also, 2-substituted quinoxaline derivatives are synthesized by dehydrogenative coupling of 1,2-diaminobenzene and 1,2-diols. In both cases, water and hydrogen gas are formed as the sole byproducts. The reactions are catalyzed by acridine-based pincer complexes of earth-abundant manganese.",

keywords = "dehydrogenative coupling, manganese, pincer, pyrazine, quinoxaline",

author = "Prosenjit Daw and Amit Kumar and Espinosa-Jalapa, {Noel Angel} and Yael Diskin-Posner and Yehoshoa Ben-David and David Milstein",

note = "Funding Information: This research was supported by the European Research Council (ERC AdG 692775). D.M. holds the Israel Matz Professorial Chair. P.D. and A.K. are thankful to the Planning and Budgeting Committee (PBC) for a postdoctoral fellowship. N. A. E.-J. thanks Mr. Armando Jinich for a postdoctoral fellowship.",

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AU - Diskin-Posner, Yael

AU - Ben-David, Yehoshoa

AU - Milstein, David

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