Chemoselective Double Allylic Substitutions with Carbon Nucleophiles: Access to Tetrahydroindoles and Tetrahydrocarbazoles

Bocheng Chen; Lucas Pagès; Cyrille Kouklovsky; Sébastien Prévost; Aurélien de la Torre

doi:10.1021/acs.joc.5c00121

Chemoselective Double Allylic Substitutions with Carbon Nucleophiles: Access to Tetrahydroindoles and Tetrahydrocarbazoles

Bocheng Chen
, Lucas Pagès
, Cyrille Kouklovsky
, Sébastien Prévost
, Aurélien de la Torre

Institut de Chimie Moléculaire et des Matériaux d'Orsay
Laboratoire de Synthèse Organique

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

Abstract

A chemoselective double allylic substitution involving two different carbon nucleophiles is described. The reaction relies on a dual catalytic approach, with a Lewis acid promoting the first allylic substitution and Pd promoting the second step. Starting from simple allylic diols, a diversity of polycyclic structures can be obtained, including tetrahydroindole, tetrahydrocarbazole, and tetrahydronaphthalene.

Original language	English
Pages (from-to)	6079-6083
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	90
Issue number	17
DOIs	https://doi.org/10.1021/acs.joc.5c00121
Publication status	Published - 2 May 2025
Externally published	Yes

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10.1021/acs.joc.5c00121

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title = "Chemoselective Double Allylic Substitutions with Carbon Nucleophiles: Access to Tetrahydroindoles and Tetrahydrocarbazoles",

abstract = "A chemoselective double allylic substitution involving two different carbon nucleophiles is described. The reaction relies on a dual catalytic approach, with a Lewis acid promoting the first allylic substitution and Pd promoting the second step. Starting from simple allylic diols, a diversity of polycyclic structures can be obtained, including tetrahydroindole, tetrahydrocarbazole, and tetrahydronaphthalene.",

author = "Bocheng Chen and Lucas Pag{\`e}s and Cyrille Kouklovsky and S{\'e}bastien Pr{\'e}vost and \{de la Torre\}, Aur{\'e}lien",

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AU - Chen, Bocheng

AU - Pagès, Lucas

AU - Kouklovsky, Cyrille

AU - Prévost, Sébastien

AU - de la Torre, Aurélien

PY - 2025/5/2

Y1 - 2025/5/2

N2 - A chemoselective double allylic substitution involving two different carbon nucleophiles is described. The reaction relies on a dual catalytic approach, with a Lewis acid promoting the first allylic substitution and Pd promoting the second step. Starting from simple allylic diols, a diversity of polycyclic structures can be obtained, including tetrahydroindole, tetrahydrocarbazole, and tetrahydronaphthalene.

AB - A chemoselective double allylic substitution involving two different carbon nucleophiles is described. The reaction relies on a dual catalytic approach, with a Lewis acid promoting the first allylic substitution and Pd promoting the second step. Starting from simple allylic diols, a diversity of polycyclic structures can be obtained, including tetrahydroindole, tetrahydrocarbazole, and tetrahydronaphthalene.

UR - https://www.scopus.com/pages/publications/105003223499

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DO - 10.1021/acs.joc.5c00121

M3 - Article

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 17

ER -

Chemoselective Double Allylic Substitutions with Carbon Nucleophiles: Access to Tetrahydroindoles and Tetrahydrocarbazoles

Abstract

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