Royal Society of Chemistry (RSC)
Organic and Biomolecular Chemistry
,  volume 18 ,  issue 42 ,  pages 8677-8685

Copper-promoted cyanoalkylation/ring-expansion of vinylcyclopropanes with α-C–H bonds in alkylnitriles toward 3,4-dihydronaphthalenes

Zan Chen 1, 2, 3, 4, 5
, 
Quan Zhou 1, 2, 3, 4, 5
, 
Qing Nan Chen 1
, 
Qing-nan Chen 1, 2, 3, 4, 5
, 
Pu Chen 1, 2, 3, 4, 5
, 
Biquan Xiong 1, 2, 3, 4, 5
, 
Yun Liang 5, 6, 7, 8, 9
, 
Kewen Tang 1, 2, 3, 4, 5
, 
Jun Xie 1, 2, 3, 4, 5
, 
Yu Liu 1, 2, 3, 4, 5, 6, 7
1
 
2
 
Department of Chemistry and Chemical Engineering
3
 
4
 
Yueyang 414006 | 
5
 
CHINA | 
6
 
7
 
Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province | 
8
 
9
 
Changsha | 
Publication type: Journal Article
Publication date: 2020-10-06
Royal Society of Chemistry (RSC)
scimago Q2
wos Q2
SJR: 0.600
CiteScore: 5.2
Impact factor: 2.7
ISSN: 14770520, 14770539
DOI:  10.1039/d0ob01864c
PubMed ID:  33078807
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
A copper-promoted oxidative cyanomethylation/ring-expansion of vinylcyclopropanes with α-C(sp3)–H bonds in alkyl nitriles is established for the generation of 1-cyanoethylated 3,4-dihydronaphthalenes. This cyanomethylation/ring-expansion involves a radical pathway and proceeds via cyanomethyl radical formation, radical addition and ring-expansion. This ring-expansion strategy offers a highly atom-economical route for the construction of nitrile-containing 3,4-dihydronaphthalenes, which can be transformed into other useful products under simple conditions.
Found 
Found 

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GOST Copy
Chen Z. et al. Copper-promoted cyanoalkylation/ring-expansion of vinylcyclopropanes with α-C–H bonds in alkylnitriles toward 3,4-dihydronaphthalenes // Organic and Biomolecular Chemistry. 2020. Vol. 18. No. 42. pp. 8677-8685.
GOST all authors (up to 50) Copy
Chen Z., Zhou Q., Chen Q. N., Chen Q., Chen P., Xiong B., Liang Y., Tang K., Xie J., Liu Yu. Copper-promoted cyanoalkylation/ring-expansion of vinylcyclopropanes with α-C–H bonds in alkylnitriles toward 3,4-dihydronaphthalenes // Organic and Biomolecular Chemistry. 2020. Vol. 18. No. 42. pp. 8677-8685.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1039/d0ob01864c
UR - https://xlink.rsc.org/?DOI=D0OB01864C
TI - Copper-promoted cyanoalkylation/ring-expansion of vinylcyclopropanes with α-C–H bonds in alkylnitriles toward 3,4-dihydronaphthalenes
T2 - Organic and Biomolecular Chemistry
AU - Chen, Zan
AU - Zhou, Quan
AU - Chen, Qing Nan
AU - Chen, Qing-nan
AU - Chen, Pu
AU - Xiong, Biquan
AU - Liang, Yun
AU - Tang, Kewen
AU - Xie, Jun
AU - Liu, Yu
PY - 2020
DA - 2020/10/06
PB - Royal Society of Chemistry (RSC)
SP - 8677-8685
IS - 42
VL - 18
PMID - 33078807
SN - 1477-0520
SN - 1477-0539
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2020_Chen,
author = {Zan Chen and Quan Zhou and Qing Nan Chen and Qing-nan Chen and Pu Chen and Biquan Xiong and Yun Liang and Kewen Tang and Jun Xie and Yu Liu},
title = {Copper-promoted cyanoalkylation/ring-expansion of vinylcyclopropanes with α-C–H bonds in alkylnitriles toward 3,4-dihydronaphthalenes},
journal = {Organic and Biomolecular Chemistry},
year = {2020},
volume = {18},
publisher = {Royal Society of Chemistry (RSC)},
month = {oct},
url = {https://xlink.rsc.org/?DOI=D0OB01864C},
number = {42},
pages = {8677--8685},
doi = {10.1039/d0ob01864c}
}
MLA
Cite this
MLA Copy
Chen, Zan, et al. “Copper-promoted cyanoalkylation/ring-expansion of vinylcyclopropanes with α-C–H bonds in alkylnitriles toward 3,4-dihydronaphthalenes.” Organic and Biomolecular Chemistry, vol. 18, no. 42, Oct. 2020, pp. 8677-8685. https://xlink.rsc.org/?DOI=D0OB01864C.