Intramolecular Alkene-Alkene Coupling via Rh(III)-Catalyzed Alkenyl sp2 C-H Functionalization: Divergent Pathways to Indene or α-Naphthol Derivatives

Manikantha Maraswami; Thomas Diggins; Jeffrey Goh; Raymond Tio; Wan Qing Renee Ong; Hajime Hirao; Teck Peng Loh

doi:10.1021/acscatal.1c03175

Intramolecular Alkene-Alkene Coupling via Rh(III)-Catalyzed Alkenyl sp² C-H Functionalization: Divergent Pathways to Indene or α-Naphthol Derivatives

Manikantha Maraswami, Thomas Diggins, Jeffrey Goh, Raymond Tio, Wan Qing Renee Ong, Hajime Hirao^*, Teck Peng Loh^*

^*Corresponding author for this work

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

9 Citations (Scopus)

Abstract

Highly selective synthesis of either indene or 1-naphthol derivatives through intramolecular alkene-alkene cross-coupling is reported. The reaction works with different alkene pairs that couple to give the corresponding products in good to satisfactory yields. The indene products of our reaction also allow further derivatization. The reaction pathway is dependent on alkene functionalities.

Original language	English
Pages (from-to)	11494-11500
Number of pages	7
Journal	ACS Catalysis
Volume	11
Issue number	18
DOIs	https://doi.org/10.1021/acscatal.1c03175
Publication status	Published - Sept 17 2021
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2021 American Chemical Society.

ASJC Scopus Subject Areas

Catalysis
General Chemistry

Keywords

alkene
C−H activation
indene
naphthol
rhodium

Access to Document

10.1021/acscatal.1c03175

Cite this

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title = "Intramolecular Alkene-Alkene Coupling via Rh(III)-Catalyzed Alkenyl sp2 C-H Functionalization: Divergent Pathways to Indene or α-Naphthol Derivatives",

abstract = "Highly selective synthesis of either indene or 1-naphthol derivatives through intramolecular alkene-alkene cross-coupling is reported. The reaction works with different alkene pairs that couple to give the corresponding products in good to satisfactory yields. The indene products of our reaction also allow further derivatization. The reaction pathway is dependent on alkene functionalities.",

keywords = "alkene, C−H activation, indene, naphthol, rhodium",

author = "Manikantha Maraswami and Thomas Diggins and Jeffrey Goh and Raymond Tio and Ong, \{Wan Qing Renee\} and Hajime Hirao and Loh, \{Teck Peng\}",

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year = "2021",

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doi = "10.1021/acscatal.1c03175",

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T1 - Intramolecular Alkene-Alkene Coupling via Rh(III)-Catalyzed Alkenyl sp2 C-H Functionalization

T2 - Divergent Pathways to Indene or α-Naphthol Derivatives

AU - Maraswami, Manikantha

AU - Diggins, Thomas

AU - Goh, Jeffrey

AU - Tio, Raymond

AU - Ong, Wan Qing Renee

AU - Hirao, Hajime

AU - Loh, Teck Peng

PY - 2021/9/17

Y1 - 2021/9/17

N2 - Highly selective synthesis of either indene or 1-naphthol derivatives through intramolecular alkene-alkene cross-coupling is reported. The reaction works with different alkene pairs that couple to give the corresponding products in good to satisfactory yields. The indene products of our reaction also allow further derivatization. The reaction pathway is dependent on alkene functionalities.

AB - Highly selective synthesis of either indene or 1-naphthol derivatives through intramolecular alkene-alkene cross-coupling is reported. The reaction works with different alkene pairs that couple to give the corresponding products in good to satisfactory yields. The indene products of our reaction also allow further derivatization. The reaction pathway is dependent on alkene functionalities.

KW - alkene

KW - C−H activation

KW - indene

KW - naphthol

KW - rhodium

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