Synthesis of electrophilic N-heterocyclic carbenes based on azahelicene

Pierpaolo Morgante; Burjor Captain; Christopher D. Chouinard; Roberto Peverati; Norito Takenaka

doi:10.1016/j.tetlet.2020.152143

Synthesis of electrophilic N-heterocyclic carbenes based on azahelicene

Pierpaolo Morgante, Burjor Captain, Christopher D. Chouinard, Roberto Peverati, Norito Takenaka

Chemistry

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

5 Scopus citations

Abstract

Helical-chiral analogues of imidazopyridine-2-yilidene were synthesized from 2-aza[6]helicene. The energies of their frontier orbitals were analyzed by the density functional theory calculations. The exceedingly large extension of NHC's π system by helicene annelation significantly enhanced the π electron-accepting properties of the carbene center while the strong σ electron-donating properties of imidazopyridine-2-yilidenes were retained.

Original language	English (US)
Article number	152143
Journal	Tetrahedron Letters
Volume	61
Issue number	30
DOIs	https://doi.org/10.1016/j.tetlet.2020.152143
State	Published - Jul 23 2020

Keywords

Catalyst design
Computational chemistry
Electronic properties
Helicene
N-heterocyclic carbenes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2020.152143

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title = "Synthesis of electrophilic N-heterocyclic carbenes based on azahelicene",

abstract = "Helical-chiral analogues of imidazopyridine-2-yilidene were synthesized from 2-aza[6]helicene. The energies of their frontier orbitals were analyzed by the density functional theory calculations. The exceedingly large extension of NHC's π system by helicene annelation significantly enhanced the π electron-accepting properties of the carbene center while the strong σ electron-donating properties of imidazopyridine-2-yilidenes were retained.",

keywords = "Catalyst design, Computational chemistry, Electronic properties, Helicene, N-heterocyclic carbenes",

author = "Pierpaolo Morgante and Burjor Captain and Chouinard, {Christopher D.} and Roberto Peverati and Norito Takenaka",

note = "Funding Information: We thank the National Science Foundation (CHE1461196), the Florida Institute of Technology, and Agilent Technologies for financial support of this work. Publisher Copyright: {\textcopyright} 2020 Elsevier Ltd Copyright: Copyright 2020 Elsevier B.V., All rights reserved.",

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doi = "10.1016/j.tetlet.2020.152143",

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T1 - Synthesis of electrophilic N-heterocyclic carbenes based on azahelicene

AU - Morgante, Pierpaolo

AU - Captain, Burjor

AU - Chouinard, Christopher D.

AU - Peverati, Roberto

AU - Takenaka, Norito

N1 - Funding Information: We thank the National Science Foundation (CHE1461196), the Florida Institute of Technology, and Agilent Technologies for financial support of this work. Publisher Copyright: © 2020 Elsevier Ltd Copyright: Copyright 2020 Elsevier B.V., All rights reserved.

PY - 2020/7/23

Y1 - 2020/7/23

N2 - Helical-chiral analogues of imidazopyridine-2-yilidene were synthesized from 2-aza[6]helicene. The energies of their frontier orbitals were analyzed by the density functional theory calculations. The exceedingly large extension of NHC's π system by helicene annelation significantly enhanced the π electron-accepting properties of the carbene center while the strong σ electron-donating properties of imidazopyridine-2-yilidenes were retained.

AB - Helical-chiral analogues of imidazopyridine-2-yilidene were synthesized from 2-aza[6]helicene. The energies of their frontier orbitals were analyzed by the density functional theory calculations. The exceedingly large extension of NHC's π system by helicene annelation significantly enhanced the π electron-accepting properties of the carbene center while the strong σ electron-donating properties of imidazopyridine-2-yilidenes were retained.

KW - Catalyst design

KW - Computational chemistry

KW - Electronic properties

KW - Helicene

KW - N-heterocyclic carbenes

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DO - 10.1016/j.tetlet.2020.152143

M3 - Article

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

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ER -

Synthesis of electrophilic N-heterocyclic carbenes based on azahelicene

Abstract

Keywords

ASJC Scopus subject areas

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