Pd(OAc)2-catalyzed carbonylative coupling of aryl iodide with ortho-haloamines in water

Pawan J. Tambade; Yogesh P. Patil; Ziyauddin S. Qureshi; Kishor P. Dhake; Bhalchandra M. Bhanage

doi:10.1080/00397911.2010.523155

Pd(OAc)₂-catalyzed carbonylative coupling of aryl iodide with ortho-haloamines in water

Pawan J. Tambade, Yogesh P. Patil, Ziyauddin S. Qureshi, Kishor P. Dhake, Bhalchandra M. Bhanage^*

^*Corresponding author for this work

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

12 Scopus citations

Abstract

The carbonylative cross coupling of aryl iodide with ortho-haloaniline to ortho-haloanilide using phosphine-free Pd(OAc)₂ catalyst in water as a reaction medium has been studied. The present protocol facilitated the reaction of o-haloanilines with a wide variety of hindered and functionalized aryl iodides, affording good yields of the desired products. The protocol was also extended for the synthesis of benzoxazoles through cyclization of ortho-haloanilide using Cu(acac)₂ catalyst.

Original language	English
Pages (from-to)	176-185
Number of pages	10
Journal	Synthetic Communications
Volume	42
Issue number	2
DOIs	https://doi.org/10.1080/00397911.2010.523155
State	Published - Jan 2012
Externally published	Yes

Bibliographical note

Funding Information:
Financial assistance from the Council of Scientific and Industrial Research (CSIR), New Delhi, India, is kindly acknowledged.

Keywords

Aryl iodides
carbonylation
cyclization
halo amines
oxazoles

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1080/00397911.2010.523155

Cite this

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title = "Pd(OAc)2-catalyzed carbonylative coupling of aryl iodide with ortho-haloamines in water",

abstract = "The carbonylative cross coupling of aryl iodide with ortho-haloaniline to ortho-haloanilide using phosphine-free Pd(OAc)2 catalyst in water as a reaction medium has been studied. The present protocol facilitated the reaction of o-haloanilines with a wide variety of hindered and functionalized aryl iodides, affording good yields of the desired products. The protocol was also extended for the synthesis of benzoxazoles through cyclization of ortho-haloanilide using Cu(acac)2 catalyst.",

keywords = "Aryl iodides, carbonylation, cyclization, halo amines, oxazoles",

author = "Tambade, \{Pawan J.\} and Patil, \{Yogesh P.\} and Qureshi, \{Ziyauddin S.\} and Dhake, \{Kishor P.\} and Bhanage, \{Bhalchandra M.\}",

note = "Funding Information: Financial assistance from the Council of Scientific and Industrial Research (CSIR), New Delhi, India, is kindly acknowledged.",

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T1 - Pd(OAc)2-catalyzed carbonylative coupling of aryl iodide with ortho-haloamines in water

AU - Tambade, Pawan J.

AU - Patil, Yogesh P.

AU - Qureshi, Ziyauddin S.

AU - Dhake, Kishor P.

AU - Bhanage, Bhalchandra M.

N1 - Funding Information: Financial assistance from the Council of Scientific and Industrial Research (CSIR), New Delhi, India, is kindly acknowledged.

PY - 2012/1

Y1 - 2012/1

N2 - The carbonylative cross coupling of aryl iodide with ortho-haloaniline to ortho-haloanilide using phosphine-free Pd(OAc)2 catalyst in water as a reaction medium has been studied. The present protocol facilitated the reaction of o-haloanilines with a wide variety of hindered and functionalized aryl iodides, affording good yields of the desired products. The protocol was also extended for the synthesis of benzoxazoles through cyclization of ortho-haloanilide using Cu(acac)2 catalyst.

AB - The carbonylative cross coupling of aryl iodide with ortho-haloaniline to ortho-haloanilide using phosphine-free Pd(OAc)2 catalyst in water as a reaction medium has been studied. The present protocol facilitated the reaction of o-haloanilines with a wide variety of hindered and functionalized aryl iodides, affording good yields of the desired products. The protocol was also extended for the synthesis of benzoxazoles through cyclization of ortho-haloanilide using Cu(acac)2 catalyst.

KW - Aryl iodides

KW - carbonylation

KW - cyclization

KW - halo amines

KW - oxazoles

UR - https://www.scopus.com/pages/publications/80052902580

U2 - 10.1080/00397911.2010.523155

DO - 10.1080/00397911.2010.523155

M3 - Article

AN - SCOPUS:80052902580

SN - 0039-7911

VL - 42

SP - 176

EP - 185

JO - Synthetic Communications

JF - Synthetic Communications

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