Palladium-Catalyzed Dialkylation of C-C Triple Bonds: Access to Multi-Functionalized Indenes

Xiao Wei Liu; Shu Sen Li; Dong Ting Dai; Meng Zhao; Cui Cui Shan; Yun He Xu; Teck Peng Loh

doi:10.1021/acs.orglett.9b01163

Palladium-Catalyzed Dialkylation of C-C Triple Bonds: Access to Multi-Functionalized Indenes

Xiao Wei Liu, Shu Sen Li, Dong Ting Dai, Meng Zhao, Cui Cui Shan, Yun He Xu^*, Teck Peng Loh

^*Corresponding author for this work

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

16 Citations (Scopus)

Abstract

A palladium-catalyzed dialkylation of 1,3-dien-5-ynes was developed using alkenyl double bonds as the initiator and terminator for the synthesis of functionalized indene derivatives. The reactions were performed under mild reaction conditions, affording the corresponding multi-substituted indene derivatives in high efficiency via unprecedented 5-endo cyclization and alkylation processes. It was found that the substituent location at the alkenyl double bond was essential for the chemoselective synthesis of the indene and naphthalene derivatives, respectively.

Original language	English
Pages (from-to)	3696-3700
Number of pages	5
Journal	Organic Letters
Volume	21
Issue number	10
DOIs	https://doi.org/10.1021/acs.orglett.9b01163
Publication status	Published - May 17 2019
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2019 American Chemical Society.

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.9b01163

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abstract = "A palladium-catalyzed dialkylation of 1,3-dien-5-ynes was developed using alkenyl double bonds as the initiator and terminator for the synthesis of functionalized indene derivatives. The reactions were performed under mild reaction conditions, affording the corresponding multi-substituted indene derivatives in high efficiency via unprecedented 5-endo cyclization and alkylation processes. It was found that the substituent location at the alkenyl double bond was essential for the chemoselective synthesis of the indene and naphthalene derivatives, respectively.",

author = "Liu, {Xiao Wei} and Li, {Shu Sen} and Dai, {Dong Ting} and Meng Zhao and Shan, {Cui Cui} and Xu, {Yun He} and Loh, {Teck Peng}",

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doi = "10.1021/acs.orglett.9b01163",

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T1 - Palladium-Catalyzed Dialkylation of C-C Triple Bonds

T2 - Access to Multi-Functionalized Indenes

AU - Liu, Xiao Wei

AU - Li, Shu Sen

AU - Dai, Dong Ting

AU - Zhao, Meng

AU - Shan, Cui Cui

AU - Xu, Yun He

AU - Loh, Teck Peng

PY - 2019/5/17

Y1 - 2019/5/17

N2 - A palladium-catalyzed dialkylation of 1,3-dien-5-ynes was developed using alkenyl double bonds as the initiator and terminator for the synthesis of functionalized indene derivatives. The reactions were performed under mild reaction conditions, affording the corresponding multi-substituted indene derivatives in high efficiency via unprecedented 5-endo cyclization and alkylation processes. It was found that the substituent location at the alkenyl double bond was essential for the chemoselective synthesis of the indene and naphthalene derivatives, respectively.

AB - A palladium-catalyzed dialkylation of 1,3-dien-5-ynes was developed using alkenyl double bonds as the initiator and terminator for the synthesis of functionalized indene derivatives. The reactions were performed under mild reaction conditions, affording the corresponding multi-substituted indene derivatives in high efficiency via unprecedented 5-endo cyclization and alkylation processes. It was found that the substituent location at the alkenyl double bond was essential for the chemoselective synthesis of the indene and naphthalene derivatives, respectively.

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JO - Organic Letters

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Palladium-Catalyzed Dialkylation of C-C Triple Bonds: Access to Multi-Functionalized Indenes

Abstract

Bibliographical note

ASJC Scopus Subject Areas

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