Rh(II)/Ag(I)-Cocatalyzed Three-Component Reaction via SN1/SN1′-Type Trapping of Oxonium Ylide with the Nicholas Intermediate

Zhenghui Kang; Jiayi Shou; Dong Xing; Wenhao Hu

doi:10.1021/acs.joc.0c01162

Rh(II)/Ag(I)-Cocatalyzed Three-Component Reaction via S_N1/S_N1′-Type Trapping of Oxonium Ylide with the Nicholas Intermediate

Zhenghui Kang
, Jiayi Shou
, Dong Xing
, Wenhao Hu^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

Sun Yat-Sen University
East China Normal University

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

10 Scopus citations

Abstract

A Rh(II)/Ag(I)-cocatalyzed three-component reaction of propargylic alcohol-Co2(CO)6 complexes with diazo compounds and benzyl alcohols is described, which represents the first trapping process of oxonium ylides with carbocations via the SN1/SN1′-type pathway. This transformation provides an efficient approach for construction of dicobalt hexacarbonyl-complexed 3,3-disubstituted oxindoles. Further derivatization of the product, initiated by the deprivation of the dicobalt species, gives the 3,3-disubstituted oxindoles with the ene alkynyl group and the privileged spirooxindole-vinyldihydropyran structure.

Original language	English
Pages (from-to)	9850-9862
Number of pages	13
Journal	Journal of Organic Chemistry
Volume	85
Issue number	15
DOIs	https://doi.org/10.1021/acs.joc.0c01162
State	Published - 7 Aug 2020

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title = "Rh(II)/Ag(I)-Cocatalyzed Three-Component Reaction via SN1/SN1′-Type Trapping of Oxonium Ylide with the Nicholas Intermediate",

abstract = "A Rh(II)/Ag(I)-cocatalyzed three-component reaction of propargylic alcohol-Co2(CO)6 complexes with diazo compounds and benzyl alcohols is described, which represents the first trapping process of oxonium ylides with carbocations via the SN1/SN1′-type pathway. This transformation provides an efficient approach for construction of dicobalt hexacarbonyl-complexed 3,3-disubstituted oxindoles. Further derivatization of the product, initiated by the deprivation of the dicobalt species, gives the 3,3-disubstituted oxindoles with the ene alkynyl group and the privileged spirooxindole-vinyldihydropyran structure.",

author = "Zhenghui Kang and Jiayi Shou and Dong Xing and Wenhao Hu",

note = "Publisher Copyright: Copyright {\textcopyright} 2020 American Chemical Society.",

year = "2020",

month = aug,

day = "7",

doi = "10.1021/acs.joc.0c01162",

language = "英语",

volume = "85",

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journal = "Journal of Organic Chemistry",

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publisher = "American Chemical Society",

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TY - JOUR

T1 - Rh(II)/Ag(I)-Cocatalyzed Three-Component Reaction via SN1/SN1′-Type Trapping of Oxonium Ylide with the Nicholas Intermediate

AU - Kang, Zhenghui

AU - Shou, Jiayi

AU - Xing, Dong

AU - Hu, Wenhao

PY - 2020/8/7

Y1 - 2020/8/7

N2 - A Rh(II)/Ag(I)-cocatalyzed three-component reaction of propargylic alcohol-Co2(CO)6 complexes with diazo compounds and benzyl alcohols is described, which represents the first trapping process of oxonium ylides with carbocations via the SN1/SN1′-type pathway. This transformation provides an efficient approach for construction of dicobalt hexacarbonyl-complexed 3,3-disubstituted oxindoles. Further derivatization of the product, initiated by the deprivation of the dicobalt species, gives the 3,3-disubstituted oxindoles with the ene alkynyl group and the privileged spirooxindole-vinyldihydropyran structure.

AB - A Rh(II)/Ag(I)-cocatalyzed three-component reaction of propargylic alcohol-Co2(CO)6 complexes with diazo compounds and benzyl alcohols is described, which represents the first trapping process of oxonium ylides with carbocations via the SN1/SN1′-type pathway. This transformation provides an efficient approach for construction of dicobalt hexacarbonyl-complexed 3,3-disubstituted oxindoles. Further derivatization of the product, initiated by the deprivation of the dicobalt species, gives the 3,3-disubstituted oxindoles with the ene alkynyl group and the privileged spirooxindole-vinyldihydropyran structure.

UR - https://www.scopus.com/pages/publications/85091451984

U2 - 10.1021/acs.joc.0c01162

DO - 10.1021/acs.joc.0c01162

M3 - 文章

AN - SCOPUS:85091451984

SN - 0022-3263

VL - 85

SP - 9850

EP - 9862

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 15

ER -

Rh(II)/Ag(I)-Cocatalyzed Three-Component Reaction via S_N1/S_N1′-Type Trapping of Oxonium Ylide with the Nicholas Intermediate

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