Preparation of 2-(2-(dicyclohexylphosphino)phenyl)-1-methyl-1h-indole (CM-phos)

Shun Man Wong; On Ying Yuen; Pui Ying Choy; Chau Ming So; Fuk Yee Kwong

doi:10.1002/0471264229.os093.02

Preparation of 2-(2-(dicyclohexylphosphino)phenyl)-1-methyl-1h-indole (CM-phos)

Shun Man Wong, On Ying Yuen, Pui Ying Choy, Chau Ming So, Fuk Yee Kwong

Research output: Journal article publication › Journal article › Academic research › peer-review

3 Citations (Scopus)

Abstract

The article describes the preparation of 2-(2-(Dicyclohexylphosphino) phenyl)-1-methyl-1H-indole (CM-phos).We selected the Fischer indole synthesis as our primary tool to synthesize the indole templates from phenylhydrazine and 2’-bromoacetophenone. With the methylated ligand precursor, CM-phos could be afforded easily by lithiation and subsequently trapping with chlorodicyclohexylphosphine. It should be noted that CM-phos in combination with the precatalyst palladium(II) acetate is highly active and effective in amination and Suzuki cross-coupling reaction of aryl mesylates.

Original language	English
Journal	Organic Syntheses
Volume	93
DOIs	https://doi.org/10.1002/0471264229.os093.02
Publication status	Published - 1 Jan 2016

Keywords

Chemical-specific hazards
CM-phos
Fischer indole synthesis
Ligand design
Metal-catalyzed coupling reactions

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

More information

10.1002/0471264229.os093.02

Cite this

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title = "Preparation of 2-(2-(dicyclohexylphosphino)phenyl)-1-methyl-1h-indole (CM-phos)",

abstract = "The article describes the preparation of 2-(2-(Dicyclohexylphosphino) phenyl)-1-methyl-1H-indole (CM-phos).We selected the Fischer indole synthesis as our primary tool to synthesize the indole templates from phenylhydrazine and 2{\textquoteright}-bromoacetophenone. With the methylated ligand precursor, CM-phos could be afforded easily by lithiation and subsequently trapping with chlorodicyclohexylphosphine. It should be noted that CM-phos in combination with the precatalyst palladium(II) acetate is highly active and effective in amination and Suzuki cross-coupling reaction of aryl mesylates.",

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doi = "10.1002/0471264229.os093.02",

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AU - Wong, Shun Man

AU - Yuen, On Ying

AU - Choy, Pui Ying

AU - So, Chau Ming

AU - Kwong, Fuk Yee

PY - 2016/1/1

Y1 - 2016/1/1

N2 - The article describes the preparation of 2-(2-(Dicyclohexylphosphino) phenyl)-1-methyl-1H-indole (CM-phos).We selected the Fischer indole synthesis as our primary tool to synthesize the indole templates from phenylhydrazine and 2’-bromoacetophenone. With the methylated ligand precursor, CM-phos could be afforded easily by lithiation and subsequently trapping with chlorodicyclohexylphosphine. It should be noted that CM-phos in combination with the precatalyst palladium(II) acetate is highly active and effective in amination and Suzuki cross-coupling reaction of aryl mesylates.

AB - The article describes the preparation of 2-(2-(Dicyclohexylphosphino) phenyl)-1-methyl-1H-indole (CM-phos).We selected the Fischer indole synthesis as our primary tool to synthesize the indole templates from phenylhydrazine and 2’-bromoacetophenone. With the methylated ligand precursor, CM-phos could be afforded easily by lithiation and subsequently trapping with chlorodicyclohexylphosphine. It should be noted that CM-phos in combination with the precatalyst palladium(II) acetate is highly active and effective in amination and Suzuki cross-coupling reaction of aryl mesylates.

KW - Chemical-specific hazards

KW - CM-phos

KW - Fischer indole synthesis

KW - Ligand design

KW - Metal-catalyzed coupling reactions

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DO - 10.1002/0471264229.os093.02

M3 - Journal article

AN - SCOPUS:85054793621

SN - 0078-6209

VL - 93

JO - Organic Syntheses

JF - Organic Syntheses

ER -

Preparation of 2-(2-(dicyclohexylphosphino)phenyl)-1-methyl-1h-indole (CM-phos)

Abstract

Keywords

ASJC Scopus subject areas

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