An efficient, mild, and selective Ullmann-type N-arylation of indoles catalyzed by copper(I) complex

R. Koteshwar Rao; Ajay B. Naidu; E. A. Jaseer; Govindasamy Sekar

doi:10.1016/j.tet.2009.03.061

An efficient, mild, and selective Ullmann-type N-arylation of indoles catalyzed by copper(I) complex

R. Koteshwar Rao
, Ajay B. Naidu
, E. A. Jaseer
, Govindasamy Sekar^*

^*Corresponding author for this work

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

47 Scopus citations

Abstract

A wide range of N-arylated indoles are selectively synthesized through intermolecular C(aryl)-N bond formation from the corresponding aryl iodides and indoles through Ullmann-type coupling reactions in the presence of a catalytic amount of easily available N,N,N′,N′-tetramethyl-BINAM-CuI complex under very mild reaction conditions.

Original language	English
Pages (from-to)	4619-4624
Number of pages	6
Journal	Tetrahedron
Volume	65
Issue number	23
DOIs	https://doi.org/10.1016/j.tet.2009.03.061
State	Published - 6 Jun 2009
Externally published	Yes

Bibliographical note

Funding Information:
We thank DST (Project No.: SR/S1/OC-06/2008), New Delhi for the financial support. R.K.R. and E.A.J. thank CSIR, New Delhi and A.B.N. thanks UGC, New Delhi for SRF. We thank DST, New Delhi, for the funding toward the 400 MHz NMR machine to the Department of Chemistry, IIT Madras under the IRPHA scheme and ESI-MS facility under the FIST programme.

Keywords

BINAM ligand
C-N bond formation
Copper catalyst
Coupling reaction
Ullmann coupling

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2009.03.061

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title = "An efficient, mild, and selective Ullmann-type N-arylation of indoles catalyzed by copper(I) complex",

abstract = "A wide range of N-arylated indoles are selectively synthesized through intermolecular C(aryl)-N bond formation from the corresponding aryl iodides and indoles through Ullmann-type coupling reactions in the presence of a catalytic amount of easily available N,N,N′,N′-tetramethyl-BINAM-CuI complex under very mild reaction conditions.",

keywords = "BINAM ligand, C-N bond formation, Copper catalyst, Coupling reaction, Ullmann coupling",

author = "Rao, \{R. Koteshwar\} and Naidu, \{Ajay B.\} and Jaseer, \{E. A.\} and Govindasamy Sekar",

note = "Funding Information: We thank DST (Project No.: SR/S1/OC-06/2008), New Delhi for the financial support. R.K.R. and E.A.J. thank CSIR, New Delhi and A.B.N. thanks UGC, New Delhi for SRF. We thank DST, New Delhi, for the funding toward the 400 MHz NMR machine to the Department of Chemistry, IIT Madras under the IRPHA scheme and ESI-MS facility under the FIST programme. ",

year = "2009",

month = jun,

day = "6",

doi = "10.1016/j.tet.2009.03.061",

language = "English",

volume = "65",

pages = "4619--4624",

journal = "Tetrahedron",

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TY - JOUR

T1 - An efficient, mild, and selective Ullmann-type N-arylation of indoles catalyzed by copper(I) complex

AU - Rao, R. Koteshwar

AU - Naidu, Ajay B.

AU - Jaseer, E. A.

AU - Sekar, Govindasamy

N1 - Funding Information: We thank DST (Project No.: SR/S1/OC-06/2008), New Delhi for the financial support. R.K.R. and E.A.J. thank CSIR, New Delhi and A.B.N. thanks UGC, New Delhi for SRF. We thank DST, New Delhi, for the funding toward the 400 MHz NMR machine to the Department of Chemistry, IIT Madras under the IRPHA scheme and ESI-MS facility under the FIST programme.

PY - 2009/6/6

Y1 - 2009/6/6

N2 - A wide range of N-arylated indoles are selectively synthesized through intermolecular C(aryl)-N bond formation from the corresponding aryl iodides and indoles through Ullmann-type coupling reactions in the presence of a catalytic amount of easily available N,N,N′,N′-tetramethyl-BINAM-CuI complex under very mild reaction conditions.

AB - A wide range of N-arylated indoles are selectively synthesized through intermolecular C(aryl)-N bond formation from the corresponding aryl iodides and indoles through Ullmann-type coupling reactions in the presence of a catalytic amount of easily available N,N,N′,N′-tetramethyl-BINAM-CuI complex under very mild reaction conditions.

KW - BINAM ligand

KW - C-N bond formation

KW - Copper catalyst

KW - Coupling reaction

KW - Ullmann coupling

UR - https://www.scopus.com/pages/publications/65449186160

U2 - 10.1016/j.tet.2009.03.061

DO - 10.1016/j.tet.2009.03.061

M3 - Article

AN - SCOPUS:65449186160

SN - 0040-4020

VL - 65

SP - 4619

EP - 4624

JO - Tetrahedron

JF - Tetrahedron

IS - 23

ER -

An efficient, mild, and selective Ullmann-type N-arylation of indoles catalyzed by copper(I) complex

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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