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

CHERIF ADOUAMA; BUDÉN, MARÍA E.; WALTER D. GUERRA; MARCELO PUIATTI; BENOIT JOSEPH; SILVIA M. BAROLO; ROSSI, R. A.; MAURICE MEDEBIELLE

ORGANIC LETTERS

AMER CHEMICAL SOC

Lugar: Washington; Año: 2019 vol. 21 p. 320 - 324

1523-7060

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 SNAr).