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^*

^*Corresponding author for this work

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

134 Citations (Scopus)

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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.

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 - 23 Jul 2018

Funding

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.

All Science Journal Classification (ASJC) codes

Catalysis

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ddm_acscatal.pyrazines_quinoxalinesAccepted author manuscript, 497 KBLicence: Unspecified

Cite this

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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.",

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

year = "2018",

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doi = "10.1021/acscatal.8b02208",

language = "English",

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journal = "ACS Catalysis",

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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 - Espinosa-Jalapa, Noel Angel

AU - Diskin-Posner, Yael

AU - Ben-David, Yehoshoa

AU - Milstein, David

PY - 2018/7/23

Y1 - 2018/7/23

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.

U2 - 10.1021/acscatal.8b02208

DO - 10.1021/acscatal.8b02208

M3 - Letter

AN - SCOPUS:85050738559

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

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All Science Journal Classification (ASJC) codes

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