Highly Regiocontrolled and Efficient Synthesis of Vinyl- And Allylstannanes via Lewis Acids Pd-Catalyzed Hydrostannation of Allenes: Scope and Limitations

Vladimir Gevorgyan; Jian Xiu Liu; Yoshinori Yamamoto

doi:10.1021/jo9624049

Highly Regiocontrolled and Efficient Synthesis of Vinyl- And Allylstannanes via Lewis Acids Pd-Catalyzed Hydrostannation of Allenes: Scope and Limitations

Vladimir Gevorgyan, Jian Xiu Liu, Yoshinori Yamamoto

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

44 Scopus citations

Abstract

The hydrostannation of allenes 1 with tributylstannyl hydride in the presence of B(C₆F₅)₃ catalyst produced vinylstannanes 2 regioselectiveiy, whereas the hydrostannation of 1 with tributylstannyl and triphenylstannyl hydride in the presence of Pd(PPh₃)₄ catalyst gave allylstannanes 5,6 regioand stereo (in certain cases)-selectively. The mechanisms for these catalytic reactions were proposed.

Original language	English (US)
Pages (from-to)	2963-2967
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	62
Issue number	9
DOIs	https://doi.org/10.1021/jo9624049
State	Published - 1997
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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title = "Highly Regiocontrolled and Efficient Synthesis of Vinyl- And Allylstannanes via Lewis Acids Pd-Catalyzed Hydrostannation of Allenes: Scope and Limitations",

abstract = "The hydrostannation of allenes 1 with tributylstannyl hydride in the presence of B(C6F5)3 catalyst produced vinylstannanes 2 regioselectiveiy, whereas the hydrostannation of 1 with tributylstannyl and triphenylstannyl hydride in the presence of Pd(PPh3)4 catalyst gave allylstannanes 5,6 regioand stereo (in certain cases)-selectively. The mechanisms for these catalytic reactions were proposed.",

author = "Vladimir Gevorgyan and Liu, {Jian Xiu} and Yoshinori Yamamoto",

year = "1997",

doi = "10.1021/jo9624049",

language = "English (US)",

volume = "62",

pages = "2963--2967",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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T1 - Highly Regiocontrolled and Efficient Synthesis of Vinyl- And Allylstannanes via Lewis Acids Pd-Catalyzed Hydrostannation of Allenes

T2 - Scope and Limitations

AU - Gevorgyan, Vladimir

AU - Liu, Jian Xiu

AU - Yamamoto, Yoshinori

PY - 1997

Y1 - 1997

N2 - The hydrostannation of allenes 1 with tributylstannyl hydride in the presence of B(C6F5)3 catalyst produced vinylstannanes 2 regioselectiveiy, whereas the hydrostannation of 1 with tributylstannyl and triphenylstannyl hydride in the presence of Pd(PPh3)4 catalyst gave allylstannanes 5,6 regioand stereo (in certain cases)-selectively. The mechanisms for these catalytic reactions were proposed.

AB - The hydrostannation of allenes 1 with tributylstannyl hydride in the presence of B(C6F5)3 catalyst produced vinylstannanes 2 regioselectiveiy, whereas the hydrostannation of 1 with tributylstannyl and triphenylstannyl hydride in the presence of Pd(PPh3)4 catalyst gave allylstannanes 5,6 regioand stereo (in certain cases)-selectively. The mechanisms for these catalytic reactions were proposed.

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

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ER -

Highly Regiocontrolled and Efficient Synthesis of Vinyl- And Allylstannanes via Lewis Acids Pd-Catalyzed Hydrostannation of Allenes: Scope and Limitations

Abstract

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