Ni-Catalyzed 1,5-Sigmatropic Ester Shift on Cyclopentadiene Rings: Regioselective Conversion of 5,5-Disubstituted Cyclopentadienes to CH2-Cyclopentadienes

Hongyan Bi; Jiaxin Chu; Xiao Li Zhao; Sunewang R. Wang

doi:10.1021/acs.orglett.4c00062

Ni-Catalyzed 1,5-Sigmatropic Ester Shift on Cyclopentadiene Rings: Regioselective Conversion of 5,5-Disubstituted Cyclopentadienes to CH₂-Cyclopentadienes

Hongyan Bi
, Jiaxin Chu
, Xiao Li Zhao^*
, Sunewang R. Wang^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

East China Normal University

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

7 Scopus citations

Abstract

Described herein is a nickel(II)-catalyzed regioselective rearrangement of 5,5-disubstituted cyclopentadienes to fully functionalized CH₂-cyclopentadienes via successive 1,5-sigmatropic shifts of the ester group on the quaternary carbon and hydrogen under mild basic conditions. The obtained CH₂-cyclopentadienes were also readily applied in the preparation of highly functionalized dibenzo[e,g]azulene derivatives in two steps.

Original language	English
Pages (from-to)	1437-1441
Number of pages	5
Journal	Organic Letters
Volume	26
Issue number	7
DOIs	https://doi.org/10.1021/acs.orglett.4c00062
State	Published - 23 Feb 2024

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title = "Ni-Catalyzed 1,5-Sigmatropic Ester Shift on Cyclopentadiene Rings: Regioselective Conversion of 5,5-Disubstituted Cyclopentadienes to CH2-Cyclopentadienes",

abstract = "Described herein is a nickel(II)-catalyzed regioselective rearrangement of 5,5-disubstituted cyclopentadienes to fully functionalized CH2-cyclopentadienes via successive 1,5-sigmatropic shifts of the ester group on the quaternary carbon and hydrogen under mild basic conditions. The obtained CH2-cyclopentadienes were also readily applied in the preparation of highly functionalized dibenzo[e,g]azulene derivatives in two steps.",

author = "Hongyan Bi and Jiaxin Chu and Zhao, \{Xiao Li\} and Wang, \{Sunewang R.\}",

note = "Publisher Copyright: {\textcopyright} 2024 American Chemical Society.",

year = "2024",

month = feb,

day = "23",

doi = "10.1021/acs.orglett.4c00062",

language = "英语",

volume = "26",

pages = "1437--1441",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Ni-Catalyzed 1,5-Sigmatropic Ester Shift on Cyclopentadiene Rings

T2 - Regioselective Conversion of 5,5-Disubstituted Cyclopentadienes to CH2-Cyclopentadienes

AU - Bi, Hongyan

AU - Chu, Jiaxin

AU - Zhao, Xiao Li

AU - Wang, Sunewang R.

PY - 2024/2/23

Y1 - 2024/2/23

N2 - Described herein is a nickel(II)-catalyzed regioselective rearrangement of 5,5-disubstituted cyclopentadienes to fully functionalized CH2-cyclopentadienes via successive 1,5-sigmatropic shifts of the ester group on the quaternary carbon and hydrogen under mild basic conditions. The obtained CH2-cyclopentadienes were also readily applied in the preparation of highly functionalized dibenzo[e,g]azulene derivatives in two steps.

AB - Described herein is a nickel(II)-catalyzed regioselective rearrangement of 5,5-disubstituted cyclopentadienes to fully functionalized CH2-cyclopentadienes via successive 1,5-sigmatropic shifts of the ester group on the quaternary carbon and hydrogen under mild basic conditions. The obtained CH2-cyclopentadienes were also readily applied in the preparation of highly functionalized dibenzo[e,g]azulene derivatives in two steps.

UR - https://www.scopus.com/pages/publications/85185581785

U2 - 10.1021/acs.orglett.4c00062

DO - 10.1021/acs.orglett.4c00062

M3 - 文章

C2 - 38345600

AN - SCOPUS:85185581785

SN - 1523-7060

VL - 26

SP - 1437

EP - 1441

JO - Organic Letters

JF - Organic Letters

IS - 7

ER -

Ni-Catalyzed 1,5-Sigmatropic Ester Shift on Cyclopentadiene Rings: Regioselective Conversion of 5,5-Disubstituted Cyclopentadienes to CH₂-Cyclopentadienes

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