Reaction of phIO·HBF4/silyl enol ether adduct with olefins as general approach to carbon-carbon bond formation in AdE reactions using hypervalent iodine reagents

Viktor Zhdankin; Rik Tykwinski; Ronald Caple; Bruce Berglund; Anatoly S. Koz'min; Nikolai S. Zefirov

doi:10.1016/S0040-4039(00)82158-9

Reaction of phIO·HBF₄/silyl enol ether adduct with olefins as general approach to carbon-carbon bond formation in Ad_E reactions using hypervalent iodine reagents

Viktor Zhdankin
, Rik Tykwinski
, Ronald Caple
, Bruce Berglund
, Anatoly S. Koz'min
, Nikolai S. Zefirov

Chemistry & Biochemistry

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

44 Scopus citations

Abstract

A simple method for method for new carbon-carbon bond formation in Ad_E reactions using the PhIO·HBF₄ complex and silyl enol ethers has been developed.

Original language	English (US)
Pages (from-to)	3703-3704
Number of pages	2
Journal	Tetrahedron Letters
Volume	29
Issue number	30
DOIs	https://doi.org/10.1016/S0040-4039(00)82158-9
State	Published - 1988

Bibliographical note

Funding Information:
Depending on the struoture of the alkene, three different kinds of products were obtained: functionalized alkenes (4,6), dihydrofuran (51, and 1,4-diketone (7) 141. The best yields were obtained in the reaotions of oyolohexene and alkenes activated with electron-donating substituents, such as tetramethylethylene and trimethylsilyloxy cyclohexene. In all oases iodobenzene separated from the reaotion mixture in a quantitative yield with aoetophenone, 1,4_diphenyl-1,4-butanedione, and hydroxy aoetophenone as by-products, respectively. We propose that the iodonium salt 3 is the reactive intermediate for all of the reactions. Initial eleotrophilio attaok of I+ on the double bond of the alkene followed by a reduotive elimination of Phi gives the final produots 4-6 [5]. It is worth emphasizing that the reported reactions potentially oould become a general route to new carbon-carbon bond oreation. The use of the highly electrophilio oomplex 1 opens a pathway for the generation of various alkyl aryl iodonium salts which could be used as highly reaotive reagents in eleotrophilio additions of different types. ACKNOWLND@ENTS. We wish to thank the IRKZ exohangee program for sponsoring V.V. Zhdankin’s to the University of Minnesota, Duluth. Aoknowledgment is also made to the Donors of the Petroleum Research Fund, administered by the American Chemioal Society, for partial support of this research.

Copyright:
Copyright 2014 Elsevier B.V., All rights reserved.

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@article{b6ddd166730f4d3bb782ec9224d68ee3,

title = "Reaction of phIO·HBF4/silyl enol ether adduct with olefins as general approach to carbon-carbon bond formation in AdE reactions using hypervalent iodine reagents",

abstract = "A simple method for method for new carbon-carbon bond formation in AdE reactions using the PhIO·HBF4 complex and silyl enol ethers has been developed.",

author = "Viktor Zhdankin and Rik Tykwinski and Ronald Caple and Bruce Berglund and Koz'min, \{Anatoly S.\} and Zefirov, \{Nikolai S.\}",

note = "Funding Information: Depending on the struoture of the alkene, three different kinds of products were obtained: functionalized alkenes (4,6), dihydrofuran (51, and 1,4-diketone (7) 141. The best yields were obtained in the reaotions of oyolohexene and alkenes activated with electron-donating substituents, such as tetramethylethylene and trimethylsilyloxy cyclohexene. In all oases iodobenzene separated from the reaotion mixture in a quantitative yield with aoetophenone, 1,4\_diphenyl-1,4-butanedione, and hydroxy aoetophenone as by-products, respectively. We propose that the iodonium salt 3 is the reactive intermediate for all of the reactions. Initial eleotrophilio attaok of I+ on the double bond of the alkene followed by a reduotive elimination of Phi gives the final produots 4-6 [5]. It is worth emphasizing that the reported reactions potentially oould become a general route to new carbon-carbon bond oreation. The use of the highly electrophilio oomplex 1 opens a pathway for the generation of various alkyl aryl iodonium salts which could be used as highly reaotive reagents in eleotrophilio additions of different types. ACKNOWLND@ENTS. We wish to thank the IRKZ exohangee program for sponsoring V.V. Zhdankin{\textquoteright}s to the University of Minnesota, Duluth. Aoknowledgment is also made to the Donors of the Petroleum Research Fund, administered by the American Chemioal Society, for partial support of this research. Copyright: Copyright 2014 Elsevier B.V., All rights reserved.",

year = "1988",

doi = "10.1016/S0040-4039(00)82158-9",

language = "English (US)",

volume = "29",

pages = "3703--3704",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "30",

}

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T1 - Reaction of phIO·HBF4/silyl enol ether adduct with olefins as general approach to carbon-carbon bond formation in AdE reactions using hypervalent iodine reagents

AU - Zhdankin, Viktor

AU - Tykwinski, Rik

AU - Caple, Ronald

AU - Berglund, Bruce

AU - Koz'min, Anatoly S.

AU - Zefirov, Nikolai S.

N1 - Funding Information: Depending on the struoture of the alkene, three different kinds of products were obtained: functionalized alkenes (4,6), dihydrofuran (51, and 1,4-diketone (7) 141. The best yields were obtained in the reaotions of oyolohexene and alkenes activated with electron-donating substituents, such as tetramethylethylene and trimethylsilyloxy cyclohexene. In all oases iodobenzene separated from the reaotion mixture in a quantitative yield with aoetophenone, 1,4_diphenyl-1,4-butanedione, and hydroxy aoetophenone as by-products, respectively. We propose that the iodonium salt 3 is the reactive intermediate for all of the reactions. Initial eleotrophilio attaok of I+ on the double bond of the alkene followed by a reduotive elimination of Phi gives the final produots 4-6 [5]. It is worth emphasizing that the reported reactions potentially oould become a general route to new carbon-carbon bond oreation. The use of the highly electrophilio oomplex 1 opens a pathway for the generation of various alkyl aryl iodonium salts which could be used as highly reaotive reagents in eleotrophilio additions of different types. ACKNOWLND@ENTS. We wish to thank the IRKZ exohangee program for sponsoring V.V. Zhdankin’s to the University of Minnesota, Duluth. Aoknowledgment is also made to the Donors of the Petroleum Research Fund, administered by the American Chemioal Society, for partial support of this research. Copyright: Copyright 2014 Elsevier B.V., All rights reserved.

PY - 1988

Y1 - 1988

N2 - A simple method for method for new carbon-carbon bond formation in AdE reactions using the PhIO·HBF4 complex and silyl enol ethers has been developed.

AB - A simple method for method for new carbon-carbon bond formation in AdE reactions using the PhIO·HBF4 complex and silyl enol ethers has been developed.

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