Ytterbium(III) triflate catalyzed annulation of propargylic 1,4-diols with aryl sulfonamides to give highly substituted pyrrole derivatives

Xiaoxiang Zhang; Jing Wei Teo; Dik Lung Ma; Chung Hang Leung; Philip Wai Hong Chan

doi:10.1016/j.tetlet.2014.10.042

Ytterbium(III) triflate catalyzed annulation of propargylic 1,4-diols with aryl sulfonamides to give highly substituted pyrrole derivatives

Xiaoxiang Zhang^*
, Jing Wei Teo
, Dik Lung Ma
, Chung Hang Leung
, Philip Wai Hong Chan

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

17 Citations (Scopus)

Abstract

A synthetic route to prepare highly substituted pyrrole derivatives efficiently in moderate to good yields via the Yb(OTf)₃-catalyzed cyclization of 1,4-propargylic diols with aryl sulfonamides is reported herein. The present synthetic method offers an operationally simple and convenient route to pyrroles under mild conditions that does not require the exclusion of air and moisture.

Original language	English
Pages (from-to)	6703-6707
Number of pages	5
Journal	Tetrahedron Letters
Volume	55
Issue number	49
DOIs	https://doi.org/10.1016/j.tetlet.2014.10.042
Publication status	Published - 3 Dec 2014

User-Defined Keywords

Homogeneous catalysis
Propargylic 1,4-diols
Pyrroles
Tandem reactions
Ytterbium(III) triflate

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10.1016/j.tetlet.2014.10.042

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@article{ce7e3a3e5337475d8ff9273b668d6f50,

title = "Ytterbium(III) triflate catalyzed annulation of propargylic 1,4-diols with aryl sulfonamides to give highly substituted pyrrole derivatives",

abstract = "A synthetic route to prepare highly substituted pyrrole derivatives efficiently in moderate to good yields via the Yb(OTf)3-catalyzed cyclization of 1,4-propargylic diols with aryl sulfonamides is reported herein. The present synthetic method offers an operationally simple and convenient route to pyrroles under mild conditions that does not require the exclusion of air and moisture.",

keywords = "Homogeneous catalysis, Propargylic 1,4-diols, Pyrroles, Tandem reactions, Ytterbium(III) triflate",

author = "Xiaoxiang Zhang and Teo, \{Jing Wei\} and Ma, \{Dik Lung\} and Leung, \{Chung Hang\} and Chan, \{Philip Wai Hong\}",

note = "Funding Information: This work is supported by Start-Up Grants from the School of Chemistry, Monash University and College of Science, Nanyang Technological University (NTU), and a Tier 1 Grant ( MOE2013-T1-002-035 ) from the Ministry of Education of Singapore (to P.W.H.C.), a Young National Natural Science Foundation of China Grant (No. 21302096 ), a Young Natural Science Foundation of Jiangsu Province Grant ( BK20130962 ) and a Project Fund from the Priority Academic Program Development of Jiangsu Higher Education Institutions (to X.Z.). We thank Dr. Yongxin Li (NTU) for providing the X-ray crystallographic data reported in this work.",

year = "2014",

month = dec,

day = "3",

doi = "10.1016/j.tetlet.2014.10.042",

language = "English",

volume = "55",

pages = "6703--6707",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

number = "49",

}

TY - JOUR

T1 - Ytterbium(III) triflate catalyzed annulation of propargylic 1,4-diols with aryl sulfonamides to give highly substituted pyrrole derivatives

AU - Zhang, Xiaoxiang

AU - Teo, Jing Wei

AU - Ma, Dik Lung

AU - Leung, Chung Hang

AU - Chan, Philip Wai Hong

N1 - Funding Information: This work is supported by Start-Up Grants from the School of Chemistry, Monash University and College of Science, Nanyang Technological University (NTU), and a Tier 1 Grant ( MOE2013-T1-002-035 ) from the Ministry of Education of Singapore (to P.W.H.C.), a Young National Natural Science Foundation of China Grant (No. 21302096 ), a Young Natural Science Foundation of Jiangsu Province Grant ( BK20130962 ) and a Project Fund from the Priority Academic Program Development of Jiangsu Higher Education Institutions (to X.Z.). We thank Dr. Yongxin Li (NTU) for providing the X-ray crystallographic data reported in this work.

PY - 2014/12/3

Y1 - 2014/12/3

N2 - A synthetic route to prepare highly substituted pyrrole derivatives efficiently in moderate to good yields via the Yb(OTf)3-catalyzed cyclization of 1,4-propargylic diols with aryl sulfonamides is reported herein. The present synthetic method offers an operationally simple and convenient route to pyrroles under mild conditions that does not require the exclusion of air and moisture.

AB - A synthetic route to prepare highly substituted pyrrole derivatives efficiently in moderate to good yields via the Yb(OTf)3-catalyzed cyclization of 1,4-propargylic diols with aryl sulfonamides is reported herein. The present synthetic method offers an operationally simple and convenient route to pyrroles under mild conditions that does not require the exclusion of air and moisture.

KW - Homogeneous catalysis

KW - Propargylic 1,4-diols

KW - Pyrroles

KW - Tandem reactions

KW - Ytterbium(III) triflate

UR - https://www.scopus.com/pages/publications/84910058084

U2 - 10.1016/j.tetlet.2014.10.042

DO - 10.1016/j.tetlet.2014.10.042

M3 - Journal article

AN - SCOPUS:84910058084

SN - 0040-4039

VL - 55

SP - 6703

EP - 6707

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 49

ER -

Ytterbium(III) triflate catalyzed annulation of propargylic 1,4-diols with aryl sulfonamides to give highly substituted pyrrole derivatives

Abstract

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