Palladium-Catalyzed Cycloaromatization/Alkylation of o-(Alkynyl)styrenes

Shu Sen Li; Meng Zhao; Xiao Wei Liu; Jian Lin Xu; Yun He Xu; Teck Peng Loh

doi:10.1021/acs.joc.9b01630

Palladium-Catalyzed Cycloaromatization/Alkylation of o-(Alkynyl)styrenes

Shu Sen Li, Meng Zhao, Xiao Wei Liu, Jian Lin Xu, Yun He Xu^*, Teck Peng Loh

^*Corresponding author for this work

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

7 Citations (Scopus)

Abstract

A Pd(II)-catalyzed mild and highly regioselective 6-endo cyclization/alkylation reaction of o-(alkynyl)styrenes with simple allylic alcohols has been developed. Under mild reaction conditions, the vinyl palladium species generated in situ after cyclization could insert a C-C double bond of allylic alcohol through a cross-coupling reaction and led to the formation of (alkyl)naphthalenes. This cascade cross-coupling reaction represents a direct and atom economic method for the construction of functionalized naphthalene derivatives in moderate to good yields.

Original language	English
Pages (from-to)	12848-12855
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	84
Issue number	20
DOIs	https://doi.org/10.1021/acs.joc.9b01630
Publication status	Published - Oct 18 2019
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2019 American Chemical Society.

ASJC Scopus Subject Areas

Organic Chemistry

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10.1021/acs.joc.9b01630

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abstract = "A Pd(II)-catalyzed mild and highly regioselective 6-endo cyclization/alkylation reaction of o-(alkynyl)styrenes with simple allylic alcohols has been developed. Under mild reaction conditions, the vinyl palladium species generated in situ after cyclization could insert a C-C double bond of allylic alcohol through a cross-coupling reaction and led to the formation of (alkyl)naphthalenes. This cascade cross-coupling reaction represents a direct and atom economic method for the construction of functionalized naphthalene derivatives in moderate to good yields.",

author = "Li, {Shu Sen} and Meng Zhao and Liu, {Xiao Wei} and Xu, {Jian Lin} and Xu, {Yun He} and Loh, {Teck Peng}",

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AU - Li, Shu Sen

AU - Zhao, Meng

AU - Liu, Xiao Wei

AU - Xu, Jian Lin

AU - Xu, Yun He

AU - Loh, Teck Peng

PY - 2019/10/18

Y1 - 2019/10/18

N2 - A Pd(II)-catalyzed mild and highly regioselective 6-endo cyclization/alkylation reaction of o-(alkynyl)styrenes with simple allylic alcohols has been developed. Under mild reaction conditions, the vinyl palladium species generated in situ after cyclization could insert a C-C double bond of allylic alcohol through a cross-coupling reaction and led to the formation of (alkyl)naphthalenes. This cascade cross-coupling reaction represents a direct and atom economic method for the construction of functionalized naphthalene derivatives in moderate to good yields.

AB - A Pd(II)-catalyzed mild and highly regioselective 6-endo cyclization/alkylation reaction of o-(alkynyl)styrenes with simple allylic alcohols has been developed. Under mild reaction conditions, the vinyl palladium species generated in situ after cyclization could insert a C-C double bond of allylic alcohol through a cross-coupling reaction and led to the formation of (alkyl)naphthalenes. This cascade cross-coupling reaction represents a direct and atom economic method for the construction of functionalized naphthalene derivatives in moderate to good yields.

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Palladium-Catalyzed Cycloaromatization/Alkylation of o-(Alkynyl)styrenes

Abstract

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