Radical ipso-substitution of a carbon-fluorine bond leading to fluoro-7-azaindolines and fluoro-7-azaindoles

Zhibo Liu; Ling Qin; Samir Z. Zard

doi:10.1021/ol500985f

Radical ipso-substitution of a carbon-fluorine bond leading to fluoro-7-azaindolines and fluoro-7-azaindoles

Zhibo Liu
, Ling Qin
, Samir Z. Zard

Laboratoire de Synthèse Organique

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

Abstract

Rare examples of a synthetically useful radical ipso-substitution of a carbon-fluorine bond are reported, leading to highly functionalized 5,6-difluoro-7-azaindolines. An unexpected hydrogen atom translocation and fragmentation with loss of molecular nitrogen and formation of a nitrile were observed in the case of an N-benzyl-tetrazole derivative.

Original language	English
Pages (from-to)	2704-2707
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	10
DOIs	https://doi.org/10.1021/ol500985f
Publication status	Published - 16 May 2014
Externally published	Yes

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title = "Radical ipso-substitution of a carbon-fluorine bond leading to fluoro-7-azaindolines and fluoro-7-azaindoles",

abstract = "Rare examples of a synthetically useful radical ipso-substitution of a carbon-fluorine bond are reported, leading to highly functionalized 5,6-difluoro-7-azaindolines. An unexpected hydrogen atom translocation and fragmentation with loss of molecular nitrogen and formation of a nitrile were observed in the case of an N-benzyl-tetrazole derivative.",

author = "Zhibo Liu and Ling Qin and Zard, \{Samir Z.\}",

year = "2014",

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AU - Liu, Zhibo

AU - Qin, Ling

AU - Zard, Samir Z.

PY - 2014/5/16

Y1 - 2014/5/16

N2 - Rare examples of a synthetically useful radical ipso-substitution of a carbon-fluorine bond are reported, leading to highly functionalized 5,6-difluoro-7-azaindolines. An unexpected hydrogen atom translocation and fragmentation with loss of molecular nitrogen and formation of a nitrile were observed in the case of an N-benzyl-tetrazole derivative.

AB - Rare examples of a synthetically useful radical ipso-substitution of a carbon-fluorine bond are reported, leading to highly functionalized 5,6-difluoro-7-azaindolines. An unexpected hydrogen atom translocation and fragmentation with loss of molecular nitrogen and formation of a nitrile were observed in the case of an N-benzyl-tetrazole derivative.

U2 - 10.1021/ol500985f

DO - 10.1021/ol500985f

M3 - Article

AN - SCOPUS:84900850869

SN - 1523-7060

VL - 16

SP - 2704

EP - 2707

JO - Organic Letters

JF - Organic Letters

IS - 10

ER -

Radical ipso-substitution of a carbon-fluorine bond leading to fluoro-7-azaindolines and fluoro-7-azaindoles

Abstract

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