A General Protocol for Radical Anion [3+2] Cycloaddition Enabled by Tandem Lewis Acid Photoredox Catalysis

Adrian G. Amador, Evan M. Sherbrook, Zhan Lu, Tehshik P. Yoon

Research output: Contribution to journalArticle

  • 1 Citations

Abstract

A method for intermolecular [3+2] cycloaddition between aryl cyclopropyl ketones and alkenes involving the combination of Lewis acid and photoredox catalysis is reported. In contrast to other more common methods for [3+2] cycloaddition, these conditions operate using a broad range of both electron-rich and electron-deficient reaction partners. The critical factors predicting the success of these reactions is the redox potential of the cyclopropyl ketone and the ability of the alkene to stabilize a key radical intermediate.

LanguageEnglish (US)
Article numberss-2017-m0573-op
Pages539-547
Number of pages9
JournalSynthesis (Germany)
Volume50
Issue number3
DOIs
StatePublished - Feb 1 2018

Fingerprint

Lewis Acids
Cycloaddition
Alkenes
Ketones
Catalysis
Olefins
Anions
Negative ions
Acids
Electrons
Oxidation-Reduction

Keywords

  • cycloaddition
  • cyclopentane
  • cyclopropane
  • photocatalysis
  • photoredox

PubMed: MeSH publication types

  • Journal Article

Cite this

A General Protocol for Radical Anion [3+2] Cycloaddition Enabled by Tandem Lewis Acid Photoredox Catalysis. / Amador, Adrian G.; Sherbrook, Evan M.; Lu, Zhan; Yoon, Tehshik P.

In: Synthesis (Germany), Vol. 50, No. 3, ss-2017-m0573-op, 01.02.2018, p. 539-547.

Research output: Contribution to journalArticle

Amador, Adrian G. ; Sherbrook, Evan M. ; Lu, Zhan ; Yoon, Tehshik P./ A General Protocol for Radical Anion [3+2] Cycloaddition Enabled by Tandem Lewis Acid Photoredox Catalysis. In: Synthesis (Germany). 2018 ; Vol. 50, No. 3. pp. 539-547
@article{7deff2ff2e7642e6bd1520fe35d219da,
title = "A General Protocol for Radical Anion [3+2] Cycloaddition Enabled by Tandem Lewis Acid Photoredox Catalysis",
abstract = "A method for intermolecular [3+2] cycloaddition between aryl cyclopropyl ketones and alkenes involving the combination of Lewis acid and photoredox catalysis is reported. In contrast to other more common methods for [3+2] cycloaddition, these conditions operate using a broad range of both electron-rich and electron-deficient reaction partners. The critical factors predicting the success of these reactions is the redox potential of the cyclopropyl ketone and the ability of the alkene to stabilize a key radical intermediate.",
keywords = "cycloaddition, cyclopentane, cyclopropane, photocatalysis, photoredox",
author = "Amador, {Adrian G.} and Sherbrook, {Evan M.} and Zhan Lu and Yoon, {Tehshik P.}",
year = "2018",
month = "2",
day = "1",
doi = "10.1055/s-0036-1591500",
language = "English (US)",
volume = "50",
pages = "539--547",
journal = "Synthesis",
issn = "0039-7881",
publisher = "Georg Thieme Verlag",
number = "3",

}

TY - JOUR

T1 - A General Protocol for Radical Anion [3+2] Cycloaddition Enabled by Tandem Lewis Acid Photoredox Catalysis

AU - Amador,Adrian G.

AU - Sherbrook,Evan M.

AU - Lu,Zhan

AU - Yoon,Tehshik P.

PY - 2018/2/1

Y1 - 2018/2/1

N2 - A method for intermolecular [3+2] cycloaddition between aryl cyclopropyl ketones and alkenes involving the combination of Lewis acid and photoredox catalysis is reported. In contrast to other more common methods for [3+2] cycloaddition, these conditions operate using a broad range of both electron-rich and electron-deficient reaction partners. The critical factors predicting the success of these reactions is the redox potential of the cyclopropyl ketone and the ability of the alkene to stabilize a key radical intermediate.

AB - A method for intermolecular [3+2] cycloaddition between aryl cyclopropyl ketones and alkenes involving the combination of Lewis acid and photoredox catalysis is reported. In contrast to other more common methods for [3+2] cycloaddition, these conditions operate using a broad range of both electron-rich and electron-deficient reaction partners. The critical factors predicting the success of these reactions is the redox potential of the cyclopropyl ketone and the ability of the alkene to stabilize a key radical intermediate.

KW - cycloaddition

KW - cyclopentane

KW - cyclopropane

KW - photocatalysis

KW - photoredox

UR - http://www.scopus.com/inward/record.url?scp=85031918849&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85031918849&partnerID=8YFLogxK

U2 - 10.1055/s-0036-1591500

DO - 10.1055/s-0036-1591500

M3 - Article

VL - 50

SP - 539

EP - 547

JO - Synthesis

T2 - Synthesis

JF - Synthesis

SN - 0039-7881

IS - 3

M1 - ss-2017-m0573-op

ER -