Stereocontrolled approach to bromofluoroalkenes and their use for the synthesis of tri- and tetrasubstituted fluoroalkenes

Grégory Landelle; Pier Alexandre Champagne; Xavier Barbeau; Jean François Paquin

doi:10.1021/ol8027412

Stereocontrolled approach to bromofluoroalkenes and their use for the synthesis of tri- and tetrasubstituted fluoroalkenes

Grégory Landelle, Pier Alexandre Champagne, Xavier Barbeau, Jean François Paquin

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

57 Scopus citations

Abstract

(Chemical Equation Presented) An addition/elimination reaction of organolithium reagents to silylated ββf-difluorostyrene derivatives followed by a bromination/ desilicobromination reaction provides a simple and effective synthetic approach to a wide range of bromofluoroalkenes (up to >97/3). In addition, the bromofluoroalkenes can be used in Pd-catalyzed transformations giving access to both tri- and tetrasubstituted fluoroalkenes.

Original language	English (US)
Pages (from-to)	681-684
Number of pages	4
Journal	Organic Letters
Volume	11
Issue number	3
DOIs	https://doi.org/10.1021/ol8027412
State	Published - Feb 5 2009
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/ol8027412

Cite this

@article{ee2d1684c96d442e8ea83a0bb528d6d4,

title = "Stereocontrolled approach to bromofluoroalkenes and their use for the synthesis of tri- and tetrasubstituted fluoroalkenes",

abstract = "(Chemical Equation Presented) An addition/elimination reaction of organolithium reagents to silylated ββf-difluorostyrene derivatives followed by a bromination/ desilicobromination reaction provides a simple and effective synthetic approach to a wide range of bromofluoroalkenes (up to >97/3). In addition, the bromofluoroalkenes can be used in Pd-catalyzed transformations giving access to both tri- and tetrasubstituted fluoroalkenes.",

author = "Gr{\'e}gory Landelle and Champagne, {Pier Alexandre} and Xavier Barbeau and Paquin, {Jean Fran{\c c}ois}",

year = "2009",

month = feb,

day = "5",

doi = "10.1021/ol8027412",

language = "English (US)",

volume = "11",

pages = "681--684",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "3",

}

TY - JOUR

T1 - Stereocontrolled approach to bromofluoroalkenes and their use for the synthesis of tri- and tetrasubstituted fluoroalkenes

AU - Landelle, Grégory

AU - Champagne, Pier Alexandre

AU - Barbeau, Xavier

AU - Paquin, Jean François

PY - 2009/2/5

Y1 - 2009/2/5

N2 - (Chemical Equation Presented) An addition/elimination reaction of organolithium reagents to silylated ββf-difluorostyrene derivatives followed by a bromination/ desilicobromination reaction provides a simple and effective synthetic approach to a wide range of bromofluoroalkenes (up to >97/3). In addition, the bromofluoroalkenes can be used in Pd-catalyzed transformations giving access to both tri- and tetrasubstituted fluoroalkenes.

AB - (Chemical Equation Presented) An addition/elimination reaction of organolithium reagents to silylated ββf-difluorostyrene derivatives followed by a bromination/ desilicobromination reaction provides a simple and effective synthetic approach to a wide range of bromofluoroalkenes (up to >97/3). In addition, the bromofluoroalkenes can be used in Pd-catalyzed transformations giving access to both tri- and tetrasubstituted fluoroalkenes.

UR - http://www.scopus.com/inward/record.url?scp=60849106993&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=60849106993&partnerID=8YFLogxK

U2 - 10.1021/ol8027412

DO - 10.1021/ol8027412

M3 - Article

C2 - 19143558

AN - SCOPUS:60849106993

SN - 1523-7060

VL - 11

SP - 681

EP - 684

JO - Organic Letters

JF - Organic Letters

IS - 3

ER -

Stereocontrolled approach to bromofluoroalkenes and their use for the synthesis of tri- and tetrasubstituted fluoroalkenes

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this