Room-Temperature and Transition-Metal-Free Intramolecular α-Arylation of Ketones: A Mild Access to Tetracyclic Indoles and 7-Azaindoles | Zendy

Chérif Adouama | Zendy; María E. Budén | Zendy; Walter D. Guerra | Zendy; Marcelo Puiatti | Zendy; Benoı̂t Joseph | Zendy; Silvia M. Barolo | Zendy; Roberto A. Rossi | Zendy; Maurice Médebielle | Zendy

Open Access

Room-Temperature and Transition-Metal-Free Intramolecular α-Arylation of Ketones: A Mild Access to Tetracyclic Indoles and 7-Azaindoles

Author(s) -

Chérif Adouama,

María E. Budén,

Walter D. Guerra,

Marcelo Puiatti,

Benoı̂t Joseph,

Silvia M. Barolo,

Roberto A. Rossi,

Maurice Médebielle

Publication year - 2018

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.8b03831

Subject(s) - chemistry , intramolecular force , nucleophilic aromatic substitution , combinatorial chemistry , transition metal , computational chemistry , stereochemistry , organic chemistry , catalysis , nucleophilic substitution

A novel approach for the synthesis of tetracyclic indoles and 7-azaindoles is reported. The strategy involves four steps, with a fast rt intramolecular α-arylation of ketones as key step. The reaction was inspected synthetically to achieve the synthesis of 11 novel tetracyclic structures with moderate to very good yields (39-85%). Theoretical combined with experimental studies led us to propose a probable polar mechanism (concerted S N Ar).

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