Direct Approach to 3-Fluoroindoles and 3,3-Difluoroindolines from 2,2-Difluoro-2-phenylethan-1-amines via C–H/N–H Coupling

Lanfei Zhang; Xiaofei Zhang; Yongmei Cui; Chunhao Yang

doi:10.1055/a-1509-8624

Synthesis, Table of Contents

Synthesis 2021; 53(20): 3815-3826
DOI: 10.1055/a-1509-8624

paper

Direct Approach to 3-Fluoroindoles and 3,3-Difluoroindolines from 2,2-Difluoro-2-phenylethan-1-amines via C–H/N–H Coupling

Lanfei Zhang

^aDepartment of Chemistry, Shanghai University, 99 Shang Da Road, Shanghai 200444, P. R. of China

^bState Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Science, 555 Zu Chong Zhi Road, Shanghai 201203, P. R. of China

,

Xiaofei Zhang

^bState Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Science, 555 Zu Chong Zhi Road, Shanghai 201203, P. R. of China

,

Yongmei Cui∗

^aDepartment of Chemistry, Shanghai University, 99 Shang Da Road, Shanghai 200444, P. R. of China

,

Chunhao Yang ∗

^bState Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Science, 555 Zu Chong Zhi Road, Shanghai 201203, P. R. of China

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Abstract

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Abstract

Herein, a direct method for the synthesis of 3-fluoroindoles and 3,3-difluoroindolines from easily accessible 2,2-difluoro-2-phenylethan-1-amines is presented. This protocol was performed by Pd-catalyzed direct C–H/N–H coupling and employed picolinamide as a directing group. By controlling the temperature for this transformation, various 3,3-difluoroindolines and 3-fluoroindoles could be isolated with moderate to good yields.

Key words

picolinamide - 3,3-difluoroindolines - 3-fluoroindoles - directing groups

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References

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