Cationic Ir(I)-catalyzed sp3 C-H bond alkenylation of ureas with alkynes for the synthesis of 2,3-disubstituted indoles

Takanori Shibata; Hiroyuki Hirashima; Mitsugu Kasagawa; Kyoji Tsuchikama; Kohei Endo

doi:10.1055/s-0030-1261205

Cationic Ir(I)-catalyzed sp³ C-H bond alkenylation of ureas with alkynes for the synthesis of 2,3-disubstituted indoles

Takanori Shibata^*, Hiroyuki Hirashima, Mitsugu Kasagawa, Kyoji Tsuchikama, Kohei Endo

^*Corresponding author for this work

School of Advanced Science and Engineering

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

29 Citations (Scopus)

Abstract

Secondary sp³ C-H bond activation of ureas was achieved by a cationic Ir(I)-JOSIPHOS catalyst. Regioselective C-H bond cleavage adjacent to the nitrogen atom in N-benzylureas and an N-allyl urea possessing a 2-alkynylphenyl group, and subsequent intramolecular reaction with an alkyne along with double-bond isomerization provided 2,3-disubstituted indoles.

Original language	English
Article number	U05011ST
Pages (from-to)	2171-2176
Number of pages	6
Journal	Synlett
Issue number	15
DOIs	https://doi.org/10.1055/s-0030-1261205
Publication status	Published - 2011

Keywords

C-H bond activation
directing group
indoles
iridium
ureas

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1055/s-0030-1261205

Cite this

@article{3906b041ab054858b8f997128f596397,

title = "Cationic Ir(I)-catalyzed sp3 C-H bond alkenylation of ureas with alkynes for the synthesis of 2,3-disubstituted indoles",

abstract = "Secondary sp3 C-H bond activation of ureas was achieved by a cationic Ir(I)-JOSIPHOS catalyst. Regioselective C-H bond cleavage adjacent to the nitrogen atom in N-benzylureas and an N-allyl urea possessing a 2-alkynylphenyl group, and subsequent intramolecular reaction with an alkyne along with double-bond isomerization provided 2,3-disubstituted indoles.",

keywords = "C-H bond activation, directing group, indoles, iridium, ureas",

author = "Takanori Shibata and Hiroyuki Hirashima and Mitsugu Kasagawa and Kyoji Tsuchikama and Kohei Endo",

year = "2011",

doi = "10.1055/s-0030-1261205",

language = "English",

pages = "2171--2176",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "15",

}

TY - JOUR

T1 - Cationic Ir(I)-catalyzed sp3 C-H bond alkenylation of ureas with alkynes for the synthesis of 2,3-disubstituted indoles

AU - Shibata, Takanori

AU - Hirashima, Hiroyuki

AU - Kasagawa, Mitsugu

AU - Tsuchikama, Kyoji

AU - Endo, Kohei

PY - 2011

Y1 - 2011

N2 - Secondary sp3 C-H bond activation of ureas was achieved by a cationic Ir(I)-JOSIPHOS catalyst. Regioselective C-H bond cleavage adjacent to the nitrogen atom in N-benzylureas and an N-allyl urea possessing a 2-alkynylphenyl group, and subsequent intramolecular reaction with an alkyne along with double-bond isomerization provided 2,3-disubstituted indoles.

AB - Secondary sp3 C-H bond activation of ureas was achieved by a cationic Ir(I)-JOSIPHOS catalyst. Regioselective C-H bond cleavage adjacent to the nitrogen atom in N-benzylureas and an N-allyl urea possessing a 2-alkynylphenyl group, and subsequent intramolecular reaction with an alkyne along with double-bond isomerization provided 2,3-disubstituted indoles.

KW - C-H bond activation

KW - directing group

KW - indoles

KW - iridium

KW - ureas

UR - http://www.scopus.com/inward/record.url?scp=80052670269&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=80052670269&partnerID=8YFLogxK

U2 - 10.1055/s-0030-1261205

DO - 10.1055/s-0030-1261205

M3 - Article

AN - SCOPUS:80052670269

SN - 0936-5214

SP - 2171

EP - 2176

JO - Synlett

JF - Synlett

IS - 15

M1 - U05011ST

ER -