Chemo- and Regioselective Synthesis of Alkynyl Cyclobutanes by Visible Light Photocatalysis

Chao Zhou, Tao Lei, Xiang Zhu Wei, Zan Liu, Bin Chen, Vaidhyanathan Ramamurthy, Chen Ho Tung, Li Zhu Wu

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

Here is the first visible light catalytic intermolecular cross [2 + 2] cycloaddition of enynes with alkenes to alkynyl cyclobutanes established with good functional group tolerance and high reaction efficiency and selectivity. Detailed studies reveal that enynes, including nonaromatic ones, can be sensitized by fac-Ir(ppy)3 via an energy transfer pathway. Addition of the Lewis acid PPh3AuNTf2 enables the cross photo[2 + 2] cycloaddition reaction to take place under both direct visible light irradiation or sensitization by Ru(bpy)3(PF6)2.

Original languageEnglish (US)
Pages (from-to)6808-6811
Number of pages4
JournalOrganic Letters
Volume20
Issue number21
DOIs
StatePublished - Nov 2 2018

Fingerprint

Cyclobutanes
cyclobutane
Cycloaddition
Photocatalysis
Cycloaddition Reaction
cycloaddition
Light
Lewis Acids
Energy Transfer
Alkenes
synthesis
Energy transfer
Functional groups
alkenes
selectivity
energy transfer
Irradiation
acids
irradiation
tris(2,2'-bipyridine)ruthenium II

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Chemo- and Regioselective Synthesis of Alkynyl Cyclobutanes by Visible Light Photocatalysis. / Zhou, Chao; Lei, Tao; Wei, Xiang Zhu; Liu, Zan; Chen, Bin; Ramamurthy, Vaidhyanathan; Tung, Chen Ho; Wu, Li Zhu.

In: Organic Letters, Vol. 20, No. 21, 02.11.2018, p. 6808-6811.

Research output: Contribution to journalArticle

Zhou, Chao ; Lei, Tao ; Wei, Xiang Zhu ; Liu, Zan ; Chen, Bin ; Ramamurthy, Vaidhyanathan ; Tung, Chen Ho ; Wu, Li Zhu. / Chemo- and Regioselective Synthesis of Alkynyl Cyclobutanes by Visible Light Photocatalysis. In: Organic Letters. 2018 ; Vol. 20, No. 21. pp. 6808-6811.
@article{5bfeba4048524d47938991cb90a6cf7e,
title = "Chemo- and Regioselective Synthesis of Alkynyl Cyclobutanes by Visible Light Photocatalysis",
abstract = "Here is the first visible light catalytic intermolecular cross [2 + 2] cycloaddition of enynes with alkenes to alkynyl cyclobutanes established with good functional group tolerance and high reaction efficiency and selectivity. Detailed studies reveal that enynes, including nonaromatic ones, can be sensitized by fac-Ir(ppy)3 via an energy transfer pathway. Addition of the Lewis acid PPh3AuNTf2 enables the cross photo[2 + 2] cycloaddition reaction to take place under both direct visible light irradiation or sensitization by Ru(bpy)3(PF6)2.",
author = "Chao Zhou and Tao Lei and Wei, {Xiang Zhu} and Zan Liu and Bin Chen and Vaidhyanathan Ramamurthy and Tung, {Chen Ho} and Wu, {Li Zhu}",
year = "2018",
month = "11",
day = "2",
doi = "10.1021/acs.orglett.8b02934",
language = "English (US)",
volume = "20",
pages = "6808--6811",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "21",

}

TY - JOUR

T1 - Chemo- and Regioselective Synthesis of Alkynyl Cyclobutanes by Visible Light Photocatalysis

AU - Zhou, Chao

AU - Lei, Tao

AU - Wei, Xiang Zhu

AU - Liu, Zan

AU - Chen, Bin

AU - Ramamurthy, Vaidhyanathan

AU - Tung, Chen Ho

AU - Wu, Li Zhu

PY - 2018/11/2

Y1 - 2018/11/2

N2 - Here is the first visible light catalytic intermolecular cross [2 + 2] cycloaddition of enynes with alkenes to alkynyl cyclobutanes established with good functional group tolerance and high reaction efficiency and selectivity. Detailed studies reveal that enynes, including nonaromatic ones, can be sensitized by fac-Ir(ppy)3 via an energy transfer pathway. Addition of the Lewis acid PPh3AuNTf2 enables the cross photo[2 + 2] cycloaddition reaction to take place under both direct visible light irradiation or sensitization by Ru(bpy)3(PF6)2.

AB - Here is the first visible light catalytic intermolecular cross [2 + 2] cycloaddition of enynes with alkenes to alkynyl cyclobutanes established with good functional group tolerance and high reaction efficiency and selectivity. Detailed studies reveal that enynes, including nonaromatic ones, can be sensitized by fac-Ir(ppy)3 via an energy transfer pathway. Addition of the Lewis acid PPh3AuNTf2 enables the cross photo[2 + 2] cycloaddition reaction to take place under both direct visible light irradiation or sensitization by Ru(bpy)3(PF6)2.

UR - http://www.scopus.com/inward/record.url?scp=85055912279&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85055912279&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.8b02934

DO - 10.1021/acs.orglett.8b02934

M3 - Article

VL - 20

SP - 6808

EP - 6811

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 21

ER -