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^*

^*此作品的通讯作者

化学与分子工程学院

East China Normal University

科研成果: 期刊稿件 › 文章 › 同行评审

8 引用（Scopus）

摘要

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.

源语言	英语
页（从-至）	1437-1441
页数	5
期刊	Organic Letters
卷	26
期	7
DOI	https://doi.org/10.1021/acs.orglett.4c00062
出版状态	已出版 - 23 2月 2024

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10.1021/acs.orglett.4c00062

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@article{c09025197f514869aaad06e24f3876ce,

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",

number = "7",

}

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