Stereocontrolled access to unsymmetrical 1,1 -diaryl-2-fluoroethenes

Grégory Landelle; Marc Olivier Turcotte-Savard; Judikaëlle Marterer; Pier Alexandre Champagne; Jean François Paquin

doi:10.1021/ol9022672

Stereocontrolled access to unsymmetrical 1,1 -diaryl-2-fluoroethenes

Grégory Landelle
, Marc Olivier Turcotte-Savard
, Judikaëlle Marterer
, Pier Alexandre Champagne
, Jean François Paquin

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

34 Scopus citations

Abstract

"Chemical Equation Presented" A simple and effective method for stereocontrolled preparation of 1,1-diaryl-2-fluoroethenes is reported. First, 1-aryl-1-bromo-2-fluoroethenes are generated using an addition/elimination reaction of hydride to silylated, β,β-difluorostyrene derivatives followed by a bromination/desilicobromination reaction. Subsequent Suzuki-Miyaura coupling with a variety of boronic acids gives access to the desired 1,1-diaryl-2-fluoroethenes.

Original language	English (US)
Pages (from-to)	5406-5409
Number of pages	4
Journal	Organic Letters
Volume	11
Issue number	23
DOIs	https://doi.org/10.1021/ol9022672
State	Published - Dec 3 2009
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol9022672

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title = "Stereocontrolled access to unsymmetrical 1,1 -diaryl-2-fluoroethenes",

abstract = "{"}Chemical Equation Presented{"} A simple and effective method for stereocontrolled preparation of 1,1-diaryl-2-fluoroethenes is reported. First, 1-aryl-1-bromo-2-fluoroethenes are generated using an addition/elimination reaction of hydride to silylated, β,β-difluorostyrene derivatives followed by a bromination/desilicobromination reaction. Subsequent Suzuki-Miyaura coupling with a variety of boronic acids gives access to the desired 1,1-diaryl-2-fluoroethenes.",

author = "Gr{\'e}gory Landelle and Turcotte-Savard, \{Marc Olivier\} and Judika{\"e}lle Marterer and Champagne, \{Pier Alexandre\} and Paquin, \{Jean Fran{\c c}ois\}",

year = "2009",

month = dec,

day = "3",

doi = "10.1021/ol9022672",

language = "English (US)",

volume = "11",

pages = "5406--5409",

journal = "Organic Letters",

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publisher = "American Chemical Society",

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T1 - Stereocontrolled access to unsymmetrical 1,1 -diaryl-2-fluoroethenes

AU - Landelle, Grégory

AU - Turcotte-Savard, Marc Olivier

AU - Marterer, Judikaëlle

AU - Champagne, Pier Alexandre

AU - Paquin, Jean François

PY - 2009/12/3

Y1 - 2009/12/3

N2 - "Chemical Equation Presented" A simple and effective method for stereocontrolled preparation of 1,1-diaryl-2-fluoroethenes is reported. First, 1-aryl-1-bromo-2-fluoroethenes are generated using an addition/elimination reaction of hydride to silylated, β,β-difluorostyrene derivatives followed by a bromination/desilicobromination reaction. Subsequent Suzuki-Miyaura coupling with a variety of boronic acids gives access to the desired 1,1-diaryl-2-fluoroethenes.

AB - "Chemical Equation Presented" A simple and effective method for stereocontrolled preparation of 1,1-diaryl-2-fluoroethenes is reported. First, 1-aryl-1-bromo-2-fluoroethenes are generated using an addition/elimination reaction of hydride to silylated, β,β-difluorostyrene derivatives followed by a bromination/desilicobromination reaction. Subsequent Suzuki-Miyaura coupling with a variety of boronic acids gives access to the desired 1,1-diaryl-2-fluoroethenes.

UR - https://www.scopus.com/pages/publications/72449134773

UR - https://www.scopus.com/pages/publications/72449134773#tab=citedBy

U2 - 10.1021/ol9022672

DO - 10.1021/ol9022672

M3 - Article

C2 - 19888751

AN - SCOPUS:72449134773

SN - 1523-7060

VL - 11

SP - 5406

EP - 5409

JO - Organic Letters

JF - Organic Letters

IS - 23

ER -

Stereocontrolled access to unsymmetrical 1,1 -diaryl-2-fluoroethenes

Abstract

All Science Journal Classification (ASJC) codes

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