Carbene-Catalyzed Reductive Coupling of Nitrobenzyl Bromide and Nitroalkene via the Single-Electron-Transfer (SET) Process and Formal 1,4-Addition

Yuhuang Wang; Yu Du; Xuan Huang; Xingxing Wu; Yuexia Zhang; Song Yang; Yonggui Robin Chi

doi:10.1021/acs.orglett.6b03792

Carbene-Catalyzed Reductive Coupling of Nitrobenzyl Bromide and Nitroalkene via the Single-Electron-Transfer (SET) Process and Formal 1,4-Addition

Yuhuang Wang, Yu Du, Xuan Huang, Xingxing Wu, Yuexia Zhang, Song Yang, Yonggui Robin Chi^*

^*Corresponding author for this work

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

36 Citations (Scopus)

Abstract

A carbene-catalyzed reductive 1,4-addition of nitrobenzyl bromides to nitroalkenes is disclosed. The reaction proceeds via a carbene-enabled single-electron-transfer process that generates radicals as key intermediates. The present study expands the potentials of carbene catalysis and offers unusual transformations for common substrates in organic synthesis.

Original language	English
Pages (from-to)	632-635
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	3
DOIs	https://doi.org/10.1021/acs.orglett.6b03792
Publication status	Published - Feb 3 2017
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2017 American Chemical Society.

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/acs.orglett.6b03792

Cite this

@article{ce46f4559aae4950bdeea3993f4ccf3f,

title = "Carbene-Catalyzed Reductive Coupling of Nitrobenzyl Bromide and Nitroalkene via the Single-Electron-Transfer (SET) Process and Formal 1,4-Addition",

abstract = "A carbene-catalyzed reductive 1,4-addition of nitrobenzyl bromides to nitroalkenes is disclosed. The reaction proceeds via a carbene-enabled single-electron-transfer process that generates radicals as key intermediates. The present study expands the potentials of carbene catalysis and offers unusual transformations for common substrates in organic synthesis.",

author = "Yuhuang Wang and Yu Du and Xuan Huang and Xingxing Wu and Yuexia Zhang and Song Yang and Chi, {Yonggui Robin}",

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

year = "2017",

month = feb,

day = "3",

doi = "10.1021/acs.orglett.6b03792",

language = "English",

volume = "19",

pages = "632--635",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "3",

}

TY - JOUR

T1 - Carbene-Catalyzed Reductive Coupling of Nitrobenzyl Bromide and Nitroalkene via the Single-Electron-Transfer (SET) Process and Formal 1,4-Addition

AU - Wang, Yuhuang

AU - Du, Yu

AU - Huang, Xuan

AU - Wu, Xingxing

AU - Zhang, Yuexia

AU - Yang, Song

AU - Chi, Yonggui Robin

PY - 2017/2/3

Y1 - 2017/2/3

N2 - A carbene-catalyzed reductive 1,4-addition of nitrobenzyl bromides to nitroalkenes is disclosed. The reaction proceeds via a carbene-enabled single-electron-transfer process that generates radicals as key intermediates. The present study expands the potentials of carbene catalysis and offers unusual transformations for common substrates in organic synthesis.

AB - A carbene-catalyzed reductive 1,4-addition of nitrobenzyl bromides to nitroalkenes is disclosed. The reaction proceeds via a carbene-enabled single-electron-transfer process that generates radicals as key intermediates. The present study expands the potentials of carbene catalysis and offers unusual transformations for common substrates in organic synthesis.

UR - http://www.scopus.com/inward/record.url?scp=85011422804&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85011422804&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.6b03792

DO - 10.1021/acs.orglett.6b03792

M3 - Article

C2 - 28121453

AN - SCOPUS:85011422804

SN - 1523-7060

VL - 19

SP - 632

EP - 635

JO - Organic Letters

JF - Organic Letters

IS - 3

ER -

Carbene-Catalyzed Reductive Coupling of Nitrobenzyl Bromide and Nitroalkene via the Single-Electron-Transfer (SET) Process and Formal 1,4-Addition

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Access to Document

Other files and links

Fingerprint

Cite this