Direct synthesis of fluorinated heteroarylether bioisosteres

Qianghui Zhou; Alessandro Ruffoni; Ryan Gianatassio; Yuta Fujiwara; Eran Sella; Doron Shabat; Phil S. Baran

doi:10.1002/anie.201300763

Direct synthesis of fluorinated heteroarylether bioisosteres

Qianghui Zhou, Alessandro Ruffoni, Ryan Gianatassio, Yuta Fujiwara, Eran Sella, Doron Shabat, Phil S. Baran

School of Chemistry

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

Abstract

(Bioiso)steering in a new direction: A modular synthesis of reagents (e.g. sodium difluoroethylsulfinate) that can be used for the direct incorporation of difluoroalkyl groups onto heterocycles is reported. The scope and generality of the incorporation of difluoroalkyl groups is exemplified with the difluoroethyl group and a proof of principle is shown for a general synthesis of fluorinated heteroarylether bioisosteres.

Original language	English
Pages (from-to)	3949-3952
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	14
DOIs	https://doi.org/10.1002/anie.201300763
State	Published - 2 Apr 2013

Keywords

C-H functionalization
bioisosteres
fluoroalkylation
heterocycles
synthetic methods

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10.1002/anie.201300763

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abstract = "(Bioiso)steering in a new direction: A modular synthesis of reagents (e.g. sodium difluoroethylsulfinate) that can be used for the direct incorporation of difluoroalkyl groups onto heterocycles is reported. The scope and generality of the incorporation of difluoroalkyl groups is exemplified with the difluoroethyl group and a proof of principle is shown for a general synthesis of fluorinated heteroarylether bioisosteres.",

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AU - Zhou, Qianghui

AU - Ruffoni, Alessandro

AU - Gianatassio, Ryan

AU - Fujiwara, Yuta

AU - Sella, Eran

AU - Shabat, Doron

AU - Baran, Phil S.

PY - 2013/4/2

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AB - (Bioiso)steering in a new direction: A modular synthesis of reagents (e.g. sodium difluoroethylsulfinate) that can be used for the direct incorporation of difluoroalkyl groups onto heterocycles is reported. The scope and generality of the incorporation of difluoroalkyl groups is exemplified with the difluoroethyl group and a proof of principle is shown for a general synthesis of fluorinated heteroarylether bioisosteres.

KW - C-H functionalization

KW - bioisosteres

KW - fluoroalkylation

KW - heterocycles

KW - synthetic methods

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Direct synthesis of fluorinated heteroarylether bioisosteres

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Keywords

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