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

Research output: Contribution to journalArticle

16 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 languageEnglish
Pages (from-to)7734-7741
Number of pages8
JournalACS Catalysis
Volume8
Issue number9
DOIs
Publication statusPublished - Sep 7 2018

Fingerprint

Pyrazines
Quinoxalines
Manganese
Amino alcohols
Amino Alcohols
Acridines
Derivatives
Byproducts
Hydrogen
Gases
Metals
Earth (planet)
Water
1,2-diaminobenzene

Keywords

  • dehydrogenative coupling
  • manganese
  • pincer
  • pyrazine
  • quinoxaline

ASJC Scopus subject areas

  • Catalysis

Cite this

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 journalArticle

Daw, Prosenjit ; Kumar, Amit ; Espinosa-Jalapa, Noel Angel ; Diskin-Posner, Yael ; Ben-David, Yehoshoa ; Milstein, David. / Synthesis of Pyrazines and Quinoxalines via Acceptorless Dehydrogenative Coupling Routes Catalyzed by Manganese Pincer Complexes. In: ACS Catalysis. 2018 ; Vol. 8, No. 9. pp. 7734-7741.
@article{551bf97c0a9a4772a35baca65cea9193,
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 = "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",
year = "2018",
month = "9",
day = "7",
doi = "10.1021/acscatal.8b02208",
language = "English",
volume = "8",
pages = "7734--7741",
journal = "ACS Catalysis",
issn = "2155-5435",
publisher = "American Chemical Society",
number = "9",

}

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 - 2018/9/7

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 - dehydrogenative coupling

KW - manganese

KW - pincer

KW - pyrazine

KW - quinoxaline

UR - http://www.scopus.com/inward/record.url?scp=85050738559&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85050738559&partnerID=8YFLogxK

U2 - 10.1021/acscatal.8b02208

DO - 10.1021/acscatal.8b02208

M3 - Article

VL - 8

SP - 7734

EP - 7741

JO - ACS Catalysis

JF - ACS Catalysis

SN - 2155-5435

IS - 9

ER -