Modular isoquinoline synthesis using catalytic enolate arylation and in situ functionalization

Ben S. Pilgrim; Alice E. Gatland; Charlie T. McTernan; Panayiotis A. Procopiou; Timothy J. Donohoe

doi:10.1021/ol4030309

Modular isoquinoline synthesis using catalytic enolate arylation and in situ functionalization

Ben S. Pilgrim, Alice E. Gatland, Charlie T. McTernan, Panayiotis A. Procopiou, Timothy J. Donohoe^*

^*Corresponding author for this work

Chemistry

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

53 Citations (Scopus)

Abstract

A methyl ketone, an aryl bromide, an electrophile, and ammonium chloride were combined in a four-component, three-step, and one-pot coupling procedure to furnish substituted isoquinolines in overall yields of up to 80%. This protocol utilizes the palladium catalyzed α-arylation reaction of an enolate, followed by in situ trapping with an electrophile, and aromatization with ammonium chloride. tert-Butyl cyanoacetate participated in a similar protocol; after functionalization and decarboxylation, 3-amino-4-alkyl isoquinolines were prepared in high yield.

Original language	English
Pages (from-to)	6190-6193
Number of pages	4
Journal	ORGANIC LETTERS
Volume	15
Issue number	24
DOIs	https://doi.org/10.1021/ol4030309
Publication status	Published - 20 Dec 2013

Access to Document

10.1021/ol4030309

Cite this

@article{e81eeaae2c5d4bf9bd95583cdd024d54,

title = "Modular isoquinoline synthesis using catalytic enolate arylation and in situ functionalization",

abstract = "A methyl ketone, an aryl bromide, an electrophile, and ammonium chloride were combined in a four-component, three-step, and one-pot coupling procedure to furnish substituted isoquinolines in overall yields of up to 80%. This protocol utilizes the palladium catalyzed α-arylation reaction of an enolate, followed by in situ trapping with an electrophile, and aromatization with ammonium chloride. tert-Butyl cyanoacetate participated in a similar protocol; after functionalization and decarboxylation, 3-amino-4-alkyl isoquinolines were prepared in high yield.",

author = "Pilgrim, {Ben S.} and Gatland, {Alice E.} and McTernan, {Charlie T.} and Procopiou, {Panayiotis A.} and Donohoe, {Timothy J.}",

year = "2013",

month = dec,

day = "20",

doi = "10.1021/ol4030309",

language = "English",

volume = "15",

pages = "6190--6193",

journal = "ORGANIC LETTERS",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "24",

}

TY - JOUR

T1 - Modular isoquinoline synthesis using catalytic enolate arylation and in situ functionalization

AU - Pilgrim, Ben S.

AU - Gatland, Alice E.

AU - McTernan, Charlie T.

AU - Procopiou, Panayiotis A.

AU - Donohoe, Timothy J.

PY - 2013/12/20

Y1 - 2013/12/20

N2 - A methyl ketone, an aryl bromide, an electrophile, and ammonium chloride were combined in a four-component, three-step, and one-pot coupling procedure to furnish substituted isoquinolines in overall yields of up to 80%. This protocol utilizes the palladium catalyzed α-arylation reaction of an enolate, followed by in situ trapping with an electrophile, and aromatization with ammonium chloride. tert-Butyl cyanoacetate participated in a similar protocol; after functionalization and decarboxylation, 3-amino-4-alkyl isoquinolines were prepared in high yield.

AB - A methyl ketone, an aryl bromide, an electrophile, and ammonium chloride were combined in a four-component, three-step, and one-pot coupling procedure to furnish substituted isoquinolines in overall yields of up to 80%. This protocol utilizes the palladium catalyzed α-arylation reaction of an enolate, followed by in situ trapping with an electrophile, and aromatization with ammonium chloride. tert-Butyl cyanoacetate participated in a similar protocol; after functionalization and decarboxylation, 3-amino-4-alkyl isoquinolines were prepared in high yield.

UR - http://www.scopus.com/inward/record.url?scp=84890925748&partnerID=8YFLogxK

U2 - 10.1021/ol4030309

DO - 10.1021/ol4030309

M3 - Article

AN - SCOPUS:84890925748

SN - 1523-7060

VL - 15

SP - 6190

EP - 6193

JO - ORGANIC LETTERS

JF - ORGANIC LETTERS

IS - 24

ER -

Modular isoquinoline synthesis using catalytic enolate arylation and in situ functionalization

Abstract

Access to Document

Other files and links

Fingerprint

Cite this