Regioselective Synthesis of 1,4 & 1,5-Enynes through a Ca(II)- Catalyzed Cross-Dehydrative-Coupling of Styrenes and Propargyl alcohols

Srinivasarao Yaragorla; Ravikrishna Dada; Abhishek Pareek

doi:10.1002/slct.201702278

Regioselective Synthesis of 1,4 & 1,5-Enynes through a Ca(II)- Catalyzed Cross-Dehydrative-Coupling of Styrenes and Propargyl alcohols

Srinivasarao Yaragorla, Ravikrishna Dada, Abhishek Pareek

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

11 Scopus citations

Abstract

A chemo and regioselective C(sp³) – C(sp²) and C(sp³) – C(sp³) bond formation through a Cross-Dehydrative-Coupling of styrenes and propargyl alcohols is described for the synthesis of 1,4 and 1,5-enynes. The first direct coupling of cyclic alkenes with oxindole derived propargylic alcohols is achieved for the synthesis of quaternary centered enynes under mild reaction conditions and demonstrated the gram scale synthesis. This approach meets the sustainable criterion of chemical synthesis due to its air-tolerance, atom economic (water is the only by-product), solvent free and use of less expensive and more abundant Ca(II) as the promoter.

Original language	English (US)
Pages (from-to)	495-499
Number of pages	5
Journal	ChemistrySelect
Volume	3
Issue number	2
DOIs	https://doi.org/10.1002/slct.201702278
State	Published - Jan 17 2018
Externally published	Yes

Bibliographical note

Funding Information:
RD and AP are thankful to School of Chemistry, UGC-Networking Center, University of Hyderabad for the facilities.

Publisher Copyright:
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

Calcium catalysis
Dehydrative cross coupling
Enynes
Oxindoles
Propargyl alcohols

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10.1002/slct.201702278

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title = "Regioselective Synthesis of 1,4 & 1,5-Enynes through a Ca(II)- Catalyzed Cross-Dehydrative-Coupling of Styrenes and Propargyl alcohols",

abstract = "A chemo and regioselective C(sp3) – C(sp2) and C(sp3) – C(sp3) bond formation through a Cross-Dehydrative-Coupling of styrenes and propargyl alcohols is described for the synthesis of 1,4 and 1,5-enynes. The first direct coupling of cyclic alkenes with oxindole derived propargylic alcohols is achieved for the synthesis of quaternary centered enynes under mild reaction conditions and demonstrated the gram scale synthesis. This approach meets the sustainable criterion of chemical synthesis due to its air-tolerance, atom economic (water is the only by-product), solvent free and use of less expensive and more abundant Ca(II) as the promoter.",

keywords = "Calcium catalysis, Dehydrative cross coupling, Enynes, Oxindoles, Propargyl alcohols",

author = "Srinivasarao Yaragorla and Ravikrishna Dada and Abhishek Pareek",

note = "Funding Information: RD and AP are thankful to School of Chemistry, UGC-Networking Center, University of Hyderabad for the facilities. Publisher Copyright: {\textcopyright} 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

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AU - Yaragorla, Srinivasarao

AU - Dada, Ravikrishna

AU - Pareek, Abhishek

N1 - Funding Information: RD and AP are thankful to School of Chemistry, UGC-Networking Center, University of Hyderabad for the facilities. Publisher Copyright: © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2018/1/17

Y1 - 2018/1/17

N2 - A chemo and regioselective C(sp3) – C(sp2) and C(sp3) – C(sp3) bond formation through a Cross-Dehydrative-Coupling of styrenes and propargyl alcohols is described for the synthesis of 1,4 and 1,5-enynes. The first direct coupling of cyclic alkenes with oxindole derived propargylic alcohols is achieved for the synthesis of quaternary centered enynes under mild reaction conditions and demonstrated the gram scale synthesis. This approach meets the sustainable criterion of chemical synthesis due to its air-tolerance, atom economic (water is the only by-product), solvent free and use of less expensive and more abundant Ca(II) as the promoter.

AB - A chemo and regioselective C(sp3) – C(sp2) and C(sp3) – C(sp3) bond formation through a Cross-Dehydrative-Coupling of styrenes and propargyl alcohols is described for the synthesis of 1,4 and 1,5-enynes. The first direct coupling of cyclic alkenes with oxindole derived propargylic alcohols is achieved for the synthesis of quaternary centered enynes under mild reaction conditions and demonstrated the gram scale synthesis. This approach meets the sustainable criterion of chemical synthesis due to its air-tolerance, atom economic (water is the only by-product), solvent free and use of less expensive and more abundant Ca(II) as the promoter.

KW - Calcium catalysis

KW - Dehydrative cross coupling

KW - Enynes

KW - Oxindoles

KW - Propargyl alcohols

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DO - 10.1002/slct.201702278

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Regioselective Synthesis of 1,4 & 1,5-Enynes through a Ca(II)- Catalyzed Cross-Dehydrative-Coupling of Styrenes and Propargyl alcohols

Abstract

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