Photoinduced Intermolecular [4+2] Cycloaddition Reaction for Construction of Benzobicyclo[2.2.2]octane Skeletons

Qiang Liu; Junlei Wang; Dazhi Li; Chao Yang; Wujiong Xia

doi:10.1021/acs.joc.6b02547

Photoinduced Intermolecular [4+2] Cycloaddition Reaction for Construction of Benzobicyclo[2.2.2]octane Skeletons

Qiang Liu
, Junlei Wang
, Dazhi Li
, Chao Yang^*
, Wujiong Xia

^*Corresponding author for this work

School of Chemistry and Chemical Engineering, Harbin Institute of Technology

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

6 Scopus citations

Abstract

A novel and efficient method for the synthesis of highly substituted benzobicyclo[2.2.2]octane skeletons has been explored. Under UV-light irradiation, o-divinylbenzenes underwent a pericyclic reaction to form the cyclic o-quinodimethane intermediates which were subsequently reacted with olefins through [4+2] addition to construct the benzobicyclo[2.2.2]octane skeletons in mild conditions. Gram scale reactions demonstrated the synthetic potential application of this protocol.

Original language	English
Pages (from-to)	1389-1402
Number of pages	14
Journal	Journal of Organic Chemistry
Volume	82
Issue number	3
DOIs	https://doi.org/10.1021/acs.joc.6b02547
State	Published - 3 Feb 2017
Externally published	Yes

Access to Document

10.1021/acs.joc.6b02547

Cite this

@article{f3270beb29c245f796dcbe2764e3ca40,

title = "Photoinduced Intermolecular [4+2] Cycloaddition Reaction for Construction of Benzobicyclo[2.2.2]octane Skeletons",

abstract = "A novel and efficient method for the synthesis of highly substituted benzobicyclo[2.2.2]octane skeletons has been explored. Under UV-light irradiation, o-divinylbenzenes underwent a pericyclic reaction to form the cyclic o-quinodimethane intermediates which were subsequently reacted with olefins through [4+2] addition to construct the benzobicyclo[2.2.2]octane skeletons in mild conditions. Gram scale reactions demonstrated the synthetic potential application of this protocol.",

author = "Qiang Liu and Junlei Wang and Dazhi Li and Chao Yang and Wujiong Xia",

note = "Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

year = "2017",

month = feb,

day = "3",

doi = "10.1021/acs.joc.6b02547",

language = "英语",

volume = "82",

pages = "1389--1402",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "3",

}

TY - JOUR

T1 - Photoinduced Intermolecular [4+2] Cycloaddition Reaction for Construction of Benzobicyclo[2.2.2]octane Skeletons

AU - Liu, Qiang

AU - Wang, Junlei

AU - Li, Dazhi

AU - Yang, Chao

AU - Xia, Wujiong

PY - 2017/2/3

Y1 - 2017/2/3

N2 - A novel and efficient method for the synthesis of highly substituted benzobicyclo[2.2.2]octane skeletons has been explored. Under UV-light irradiation, o-divinylbenzenes underwent a pericyclic reaction to form the cyclic o-quinodimethane intermediates which were subsequently reacted with olefins through [4+2] addition to construct the benzobicyclo[2.2.2]octane skeletons in mild conditions. Gram scale reactions demonstrated the synthetic potential application of this protocol.

AB - A novel and efficient method for the synthesis of highly substituted benzobicyclo[2.2.2]octane skeletons has been explored. Under UV-light irradiation, o-divinylbenzenes underwent a pericyclic reaction to form the cyclic o-quinodimethane intermediates which were subsequently reacted with olefins through [4+2] addition to construct the benzobicyclo[2.2.2]octane skeletons in mild conditions. Gram scale reactions demonstrated the synthetic potential application of this protocol.

UR - https://www.scopus.com/pages/publications/85011392030

U2 - 10.1021/acs.joc.6b02547

DO - 10.1021/acs.joc.6b02547

M3 - 文章

C2 - 28054780

AN - SCOPUS:85011392030

SN - 0022-3263

VL - 82

SP - 1389

EP - 1402

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 3

ER -

Photoinduced Intermolecular [4+2] Cycloaddition Reaction for Construction of Benzobicyclo[2.2.2]octane Skeletons

Abstract

Access to Document

Other files and links

Fingerprint

Cite this