Domino synthesis of 2-arylbenzo[b]furans by copper(II)-catalyzed coupling of o-iodophenols and aryl acetylenes

E. A. Jaseer; D. J.C. Prasad; Govindasamy Sekar

doi:10.1016/j.tet.2010.01.026

Domino synthesis of 2-arylbenzo[b]furans by copper(II)-catalyzed coupling of o-iodophenols and aryl acetylenes

E. A. Jaseer
, D. J.C. Prasad
, Govindasamy Sekar^*

^*Corresponding author for this work

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

65 Scopus citations

Abstract

A wide range of 2-arylbenzo[b]furans are synthesized through domino intermolecular C_(aryl)-C_(alkynyl) bond formation followed by intramolecular C_(alkynyl)-O bond forming cyclization via copper(II)-catalyzed coupling of o-iodophenols and aryl terminal acetylenes. This method requires neither expensive palladium catalyst nor oxophilic phosphine ligands, can tolerate different functional groups. The methodology is successfully utilized in formal synthesis of β-amyloid aggregation inhibitor 5-chloro-3-[4-(3-diethylaminopropoxy)benzoyl]-2-(4-methoxyphenyl) benzofuran.

Original language	English
Pages (from-to)	2077-2082
Number of pages	6
Journal	Tetrahedron
Volume	66
Issue number	11
DOIs	https://doi.org/10.1016/j.tet.2010.01.026
State	Published - 13 Mar 2010
Externally published	Yes

Bibliographical note

Funding Information:
We thank MHz NMR instrument to the department of chemistry, IIT Madras under the IRPHA scheme and ESI-MS facility under the FIST programme. DST (Project No.: SR/S1/OC-06/2008 ), New Delhi for the financial support. EAJ thanks CSIR, New Delhi for SRF and DJC Prasad thanks UGC, New Delhi. We thank DST, New Delhi, for the funding toward the 400

Keywords

Benzofuran
Copper catalyst
Coupling reaction
Diamine ligands
Sonogashira coupling

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2010.01.026

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@article{8b409328dbd145678af29f86c172cd8c,

title = "Domino synthesis of 2-arylbenzo[b]furans by copper(II)-catalyzed coupling of o-iodophenols and aryl acetylenes",

abstract = "A wide range of 2-arylbenzo[b]furans are synthesized through domino intermolecular C(aryl)-C(alkynyl) bond formation followed by intramolecular C(alkynyl)-O bond forming cyclization via copper(II)-catalyzed coupling of o-iodophenols and aryl terminal acetylenes. This method requires neither expensive palladium catalyst nor oxophilic phosphine ligands, can tolerate different functional groups. The methodology is successfully utilized in formal synthesis of β-amyloid aggregation inhibitor 5-chloro-3-[4-(3-diethylaminopropoxy)benzoyl]-2-(4-methoxyphenyl) benzofuran.",

keywords = "Benzofuran, Copper catalyst, Coupling reaction, Diamine ligands, Sonogashira coupling",

author = "Jaseer, \{E. A.\} and Prasad, \{D. J.C.\} and Govindasamy Sekar",

note = "Funding Information: We thank MHz NMR instrument to the department of chemistry, IIT Madras under the IRPHA scheme and ESI-MS facility under the FIST programme. DST (Project No.: SR/S1/OC-06/2008 ), New Delhi for the financial support. EAJ thanks CSIR, New Delhi for SRF and DJC Prasad thanks UGC, New Delhi. We thank DST, New Delhi, for the funding toward the 400 ",

year = "2010",

month = mar,

day = "13",

doi = "10.1016/j.tet.2010.01.026",

language = "English",

volume = "66",

pages = "2077--2082",

journal = "Tetrahedron",

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T1 - Domino synthesis of 2-arylbenzo[b]furans by copper(II)-catalyzed coupling of o-iodophenols and aryl acetylenes

AU - Jaseer, E. A.

AU - Prasad, D. J.C.

AU - Sekar, Govindasamy

N1 - Funding Information: We thank MHz NMR instrument to the department of chemistry, IIT Madras under the IRPHA scheme and ESI-MS facility under the FIST programme. DST (Project No.: SR/S1/OC-06/2008 ), New Delhi for the financial support. EAJ thanks CSIR, New Delhi for SRF and DJC Prasad thanks UGC, New Delhi. We thank DST, New Delhi, for the funding toward the 400

PY - 2010/3/13

Y1 - 2010/3/13

N2 - A wide range of 2-arylbenzo[b]furans are synthesized through domino intermolecular C(aryl)-C(alkynyl) bond formation followed by intramolecular C(alkynyl)-O bond forming cyclization via copper(II)-catalyzed coupling of o-iodophenols and aryl terminal acetylenes. This method requires neither expensive palladium catalyst nor oxophilic phosphine ligands, can tolerate different functional groups. The methodology is successfully utilized in formal synthesis of β-amyloid aggregation inhibitor 5-chloro-3-[4-(3-diethylaminopropoxy)benzoyl]-2-(4-methoxyphenyl) benzofuran.

AB - A wide range of 2-arylbenzo[b]furans are synthesized through domino intermolecular C(aryl)-C(alkynyl) bond formation followed by intramolecular C(alkynyl)-O bond forming cyclization via copper(II)-catalyzed coupling of o-iodophenols and aryl terminal acetylenes. This method requires neither expensive palladium catalyst nor oxophilic phosphine ligands, can tolerate different functional groups. The methodology is successfully utilized in formal synthesis of β-amyloid aggregation inhibitor 5-chloro-3-[4-(3-diethylaminopropoxy)benzoyl]-2-(4-methoxyphenyl) benzofuran.

KW - Benzofuran

KW - Copper catalyst

KW - Coupling reaction

KW - Diamine ligands

KW - Sonogashira coupling

UR - https://www.scopus.com/pages/publications/76449113927

U2 - 10.1016/j.tet.2010.01.026

DO - 10.1016/j.tet.2010.01.026

M3 - Article

AN - SCOPUS:76449113927

SN - 0040-4020

VL - 66

SP - 2077

EP - 2082

JO - Tetrahedron

JF - Tetrahedron

IS - 11

ER -

Domino synthesis of 2-arylbenzo[b]furans by copper(II)-catalyzed coupling of o-iodophenols and aryl acetylenes

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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