Red-Light-Induced N, N ′-Dipropyl-1,13-dimethoxyquinacridinium-Catalyzed [3+2] Cycloaddition of Cyclopropylamines with Alkenes or Alkynes

Savannah M. Stull; Liangyong Mei; Thomas L. Gianetti

doi:10.1055/a-1665-9220

Red-Light-Induced N, N ′-Dipropyl-1,13-dimethoxyquinacridinium-Catalyzed [3+2] Cycloaddition of Cyclopropylamines with Alkenes or Alkynes

Savannah M. Stull, Liangyong Mei, Thomas L. Gianetti

Chemistry and Biochemistry

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

15 Scopus citations

Abstract

A red-light-mediated [3+2] annulation of cyclopropylamines with akenes or alkynes in the presence of N,N'-dipropyl-1,13-dimethoxyquinacridinium is reported. An array of cyclopentane or cyclopentene derivatives with diverse functional groups have been obtained in moderate to excellent yields under mild conditions.

Original language	English (US)
Pages (from-to)	1194-1198
Number of pages	5
Journal	Synlett
Volume	33
Issue number	12
DOIs	https://doi.org/10.1055/a-1665-9220
State	Published - Jul 1 2022

Keywords

[3+2] cycloaddition
alkenes
alkynes
cyclopropylamines
dipropyldimethoxyquinacridinium
photoredox catalysis

ASJC Scopus subject areas

Organic Chemistry

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10.1055/a-1665-9220

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title = "Red-Light-Induced N, N ′-Dipropyl-1,13-dimethoxyquinacridinium-Catalyzed [3+2] Cycloaddition of Cyclopropylamines with Alkenes or Alkynes",

abstract = "A red-light-mediated [3+2] annulation of cyclopropylamines with akenes or alkynes in the presence of N,N'-dipropyl-1,13-dimethoxyquinacridinium is reported. An array of cyclopentane or cyclopentene derivatives with diverse functional groups have been obtained in moderate to excellent yields under mild conditions.",

keywords = "[3+2] cycloaddition, alkenes, alkynes, cyclopropylamines, dipropyldimethoxyquinacridinium, photoredox catalysis",

author = "Stull, {Savannah M.} and Liangyong Mei and Gianetti, {Thomas L.}",

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T1 - Red-Light-Induced N, N ′-Dipropyl-1,13-dimethoxyquinacridinium-Catalyzed [3+2] Cycloaddition of Cyclopropylamines with Alkenes or Alkynes

AU - Stull, Savannah M.

AU - Mei, Liangyong

AU - Gianetti, Thomas L.

PY - 2022/7/1

Y1 - 2022/7/1

N2 - A red-light-mediated [3+2] annulation of cyclopropylamines with akenes or alkynes in the presence of N,N'-dipropyl-1,13-dimethoxyquinacridinium is reported. An array of cyclopentane or cyclopentene derivatives with diverse functional groups have been obtained in moderate to excellent yields under mild conditions.

AB - A red-light-mediated [3+2] annulation of cyclopropylamines with akenes or alkynes in the presence of N,N'-dipropyl-1,13-dimethoxyquinacridinium is reported. An array of cyclopentane or cyclopentene derivatives with diverse functional groups have been obtained in moderate to excellent yields under mild conditions.

KW - [3+2] cycloaddition

KW - alkenes

KW - alkynes

KW - cyclopropylamines

KW - dipropyldimethoxyquinacridinium

KW - photoredox catalysis

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M3 - Article

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SN - 0936-5214

VL - 33

SP - 1194

EP - 1198

JO - Synlett

JF - Synlett

IS - 12

ER -

Red-Light-Induced N, N ′-Dipropyl-1,13-dimethoxyquinacridinium-Catalyzed [3+2] Cycloaddition of Cyclopropylamines with Alkenes or Alkynes

Abstract

Keywords

ASJC Scopus subject areas

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