New Heteroannulation Reactions of N-Alkoxybenzamides by Pd(II) Catalyzed C-H Activation

Joe W. Wrigglesworth; Brian Cox; Guy C. Lloyd-Jones; Kevin I. Booker-Milburn

doi:10.1021/ol202187h

New Heteroannulation Reactions of N-Alkoxybenzamides by Pd(II) Catalyzed C-H Activation

Joe W. Wrigglesworth, Brian Cox, Guy C. Lloyd-Jones, Kevin I. Booker-Milburn

Research output: Contribution to journal › Article (Academic Journal) › peer-review

153 Citations (Scopus)

Abstract

A new palladium(II) catalyzed methodology for the direct synthesis of alkylidene isoindolinones from Al-alkoxybenzamides is presented. Isoindolinone formation proceeds through a highly efficient and E-selective C-H activation/Heck/Aza-Wacker sequence. Substoichiometric amounts of benzoquinone can be employed in a cooperative oxidation system with O-2, leading to facile purification of products. Modification of the reaction conditions provides a general route to substituted phthalimides by carbonylation with CO. Both systems were found to tolerate a wide range of functionality.

Original language	English
Pages (from-to)	5326-5329
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	19
DOIs	https://doi.org/10.1021/ol202187h
Publication status	Published - 7 Oct 2011

Access to Document

10.1021/ol202187h

Cite this

@article{ccf9fc1f9c1744018fae4fd289dd7193,

title = "New Heteroannulation Reactions of N-Alkoxybenzamides by Pd(II) Catalyzed C-H Activation",

abstract = "A new palladium(II) catalyzed methodology for the direct synthesis of alkylidene isoindolinones from Al-alkoxybenzamides is presented. Isoindolinone formation proceeds through a highly efficient and E-selective C-H activation/Heck/Aza-Wacker sequence. Substoichiometric amounts of benzoquinone can be employed in a cooperative oxidation system with O-2, leading to facile purification of products. Modification of the reaction conditions provides a general route to substituted phthalimides by carbonylation with CO. Both systems were found to tolerate a wide range of functionality.",

author = "Wrigglesworth, {Joe W.} and Brian Cox and Lloyd-Jones, {Guy C.} and Booker-Milburn, {Kevin I.}",

year = "2011",

month = oct,

day = "7",

doi = "10.1021/ol202187h",

language = "English",

volume = "13",

pages = "5326--5329",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "19",

}

TY - JOUR

T1 - New Heteroannulation Reactions of N-Alkoxybenzamides by Pd(II) Catalyzed C-H Activation

AU - Wrigglesworth, Joe W.

AU - Cox, Brian

AU - Lloyd-Jones, Guy C.

AU - Booker-Milburn, Kevin I.

PY - 2011/10/7

Y1 - 2011/10/7

N2 - A new palladium(II) catalyzed methodology for the direct synthesis of alkylidene isoindolinones from Al-alkoxybenzamides is presented. Isoindolinone formation proceeds through a highly efficient and E-selective C-H activation/Heck/Aza-Wacker sequence. Substoichiometric amounts of benzoquinone can be employed in a cooperative oxidation system with O-2, leading to facile purification of products. Modification of the reaction conditions provides a general route to substituted phthalimides by carbonylation with CO. Both systems were found to tolerate a wide range of functionality.

AB - A new palladium(II) catalyzed methodology for the direct synthesis of alkylidene isoindolinones from Al-alkoxybenzamides is presented. Isoindolinone formation proceeds through a highly efficient and E-selective C-H activation/Heck/Aza-Wacker sequence. Substoichiometric amounts of benzoquinone can be employed in a cooperative oxidation system with O-2, leading to facile purification of products. Modification of the reaction conditions provides a general route to substituted phthalimides by carbonylation with CO. Both systems were found to tolerate a wide range of functionality.

U2 - 10.1021/ol202187h

DO - 10.1021/ol202187h

M3 - Article (Academic Journal)

C2 - 21910404

VL - 13

SP - 5326

EP - 5329

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 19

ER -