Cobalt(III)-Catalyzed Construction of Benzofurans, Benzofuranones and One-Pot Orthogonal C−H Functionalizations to Access Polysubstituted Benzofurans

Sourav Sekhar Bera; Suvankar Debbarma; Sripati Jana; Modhu Sudan Maji

doi:10.1002/adsc.201800298

Cobalt(III)-Catalyzed Construction of Benzofurans, Benzofuranones and One-Pot Orthogonal C−H Functionalizations to Access Polysubstituted Benzofurans

Sourav Sekhar Bera, Suvankar Debbarma, Sripati Jana, Modhu Sudan Maji

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

25 Citations (Scopus)

Abstract

Benzofuran and benzofuranone derivatives have been synthesized through exclusive 5-exo-dig intramolecular hydroarylation using the amide-directed, cost-effective, high-valent Cp*Co^III-catalytic system. Challenging one-pot, orthogonal C−H functionalizations using two different electrophiles are also reported to afford polysubstituted benzofurans. Several valuable functional group interconversions along with removal of the amide directing group provide a route to access several diversely functionalized benzofurans. The mechanistic study suggests a reversible cobaltation step is operative here. (Figure presented.).

Original language	English
Pages (from-to)	2204-2210
Number of pages	7
Journal	Advanced Synthesis and Catalysis
Volume	360
Issue number	11
DOIs	https://doi.org/10.1002/adsc.201800298
Publication status	Published - 2018 Jun 5
Externally published	Yes

Keywords

benzofuran
benzofuranone
cobalt
intramolecular
orthogonal C−H activation

ASJC Scopus subject areas

Catalysis
Organic Chemistry

Access to Document

10.1002/adsc.201800298

Cite this

@article{7474300300434d4fb6941bc16863cf6c,

title = "Cobalt(III)-Catalyzed Construction of Benzofurans, Benzofuranones and One-Pot Orthogonal C−H Functionalizations to Access Polysubstituted Benzofurans",

abstract = "Benzofuran and benzofuranone derivatives have been synthesized through exclusive 5-exo-dig intramolecular hydroarylation using the amide-directed, cost-effective, high-valent Cp*CoIII-catalytic system. Challenging one-pot, orthogonal C−H functionalizations using two different electrophiles are also reported to afford polysubstituted benzofurans. Several valuable functional group interconversions along with removal of the amide directing group provide a route to access several diversely functionalized benzofurans. The mechanistic study suggests a reversible cobaltation step is operative here. (Figure presented.).",

keywords = "benzofuran, benzofuranone, cobalt, intramolecular, orthogonal C−H activation",

author = "Bera, {Sourav Sekhar} and Suvankar Debbarma and Sripati Jana and Maji, {Modhu Sudan}",

note = "Funding Information: M.S.M. gratefully acknowledges SERB, Department of Science and Technology (DST), New Delhi, India (Sanction No. EMR/2015/ 000994), and IIT Kharagpur (ISIRD grant) for funding. We thank DST (Sanction No. SR/FST/CSII-026/ 2013) for 500 MHz NMR facility at IIT Kharagpur. S.S.B. thanks CSIR India and S.D. thanks IIT Kharagpur for fellowship. Publisher Copyright: {\textcopyright} 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2018",

month = jun,

day = "5",

doi = "10.1002/adsc.201800298",

language = "English",

volume = "360",

pages = "2204--2210",

journal = "Advanced Synthesis and Catalysis",

issn = "1615-4150",

publisher = "Wiley-VCH Verlag",

number = "11",

}

TY - JOUR

T1 - Cobalt(III)-Catalyzed Construction of Benzofurans, Benzofuranones and One-Pot Orthogonal C−H Functionalizations to Access Polysubstituted Benzofurans

AU - Bera, Sourav Sekhar

AU - Debbarma, Suvankar

AU - Jana, Sripati

AU - Maji, Modhu Sudan

N1 - Funding Information: M.S.M. gratefully acknowledges SERB, Department of Science and Technology (DST), New Delhi, India (Sanction No. EMR/2015/ 000994), and IIT Kharagpur (ISIRD grant) for funding. We thank DST (Sanction No. SR/FST/CSII-026/ 2013) for 500 MHz NMR facility at IIT Kharagpur. S.S.B. thanks CSIR India and S.D. thanks IIT Kharagpur for fellowship. Publisher Copyright: © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2018/6/5

Y1 - 2018/6/5

N2 - Benzofuran and benzofuranone derivatives have been synthesized through exclusive 5-exo-dig intramolecular hydroarylation using the amide-directed, cost-effective, high-valent Cp*CoIII-catalytic system. Challenging one-pot, orthogonal C−H functionalizations using two different electrophiles are also reported to afford polysubstituted benzofurans. Several valuable functional group interconversions along with removal of the amide directing group provide a route to access several diversely functionalized benzofurans. The mechanistic study suggests a reversible cobaltation step is operative here. (Figure presented.).

AB - Benzofuran and benzofuranone derivatives have been synthesized through exclusive 5-exo-dig intramolecular hydroarylation using the amide-directed, cost-effective, high-valent Cp*CoIII-catalytic system. Challenging one-pot, orthogonal C−H functionalizations using two different electrophiles are also reported to afford polysubstituted benzofurans. Several valuable functional group interconversions along with removal of the amide directing group provide a route to access several diversely functionalized benzofurans. The mechanistic study suggests a reversible cobaltation step is operative here. (Figure presented.).

KW - benzofuran

KW - benzofuranone

KW - cobalt

KW - intramolecular

KW - orthogonal C−H activation

UR - http://www.scopus.com/inward/record.url?scp=85047961392&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85047961392&partnerID=8YFLogxK

U2 - 10.1002/adsc.201800298

DO - 10.1002/adsc.201800298

M3 - Article

AN - SCOPUS:85047961392

SN - 1615-4150

VL - 360

SP - 2204

EP - 2210

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 11

ER -

Cobalt(III)-Catalyzed Construction of Benzofurans, Benzofuranones and One-Pot Orthogonal C−H Functionalizations to Access Polysubstituted Benzofurans

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this