Synthesis of pyrazines and quinoxalines via acceptorless dehydrogenative coupling routes catalyzed by manganese pincer complexes

Prosenjit Daw; Amit Kumar; Noel A. E. 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 A. E. Jalapa, Yael Diskin-Posner, Yehoshoa Ben-David, David Milstein

School of Chemistry

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

130 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
Journal	ACS Catalysis
Volume	8
Issue number	9
Early online date	23 Jul 2018
DOIs	https://doi.org/10.1021/acscatal.8b02208
Publication status	Published - 7 Sept 2018

Keywords

Manganese
Pincer
Pyrazine
Quinoxaline
Dehydrogenative coupling

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10.1021/acscatal.8b02208

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title = "Synthesis of pyrazines and quinoxalines via acceptorless dehydrogenative coupling routes catalyzed by manganese pincer complexes",

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 = "Manganese, Pincer, Pyrazine, Quinoxaline, Dehydrogenative coupling",

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

note = "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.",

year = "2018",

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day = "7",

doi = "10.1021/acscatal.8b02208",

language = "English",

volume = "8",

pages = "7734--7741",

journal = "ACS Catalysis",

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publisher = "American Chemical Society (ACS)",

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TY - JOUR

T1 - Synthesis of pyrazines and quinoxalines via acceptorless dehydrogenative coupling routes catalyzed by manganese pincer complexes

AU - Daw, Prosenjit

AU - Kumar, Amit

AU - Jalapa, Noel A. E.

AU - Diskin-Posner, Yael

AU - Ben-David, Yehoshoa

AU - Milstein, David

N1 - 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.

PY - 2018/9/7

Y1 - 2018/9/7

N2 - 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.

AB - 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.

KW - Manganese

KW - Pincer

KW - Pyrazine

KW - Quinoxaline

KW - Dehydrogenative coupling

U2 - 10.1021/acscatal.8b02208

DO - 10.1021/acscatal.8b02208

M3 - Article

SN - 2155-5435

VL - 8

SP - 7734

EP - 7741

JO - ACS Catalysis

JF - ACS Catalysis

IS - 9

ER -

Synthesis of pyrazines and quinoxalines via acceptorless dehydrogenative coupling routes catalyzed by manganese pincer complexes

Abstract

Keywords

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