Cu(I)-Catalyzed Three-Component Reaction of α-Diazo Amide with Terminal Alkyne and Isatin Ketimine via Electrophilic Trapping of Active Alkynoate-Copper Intermediate

Jiuwei Che; Alavala Gopi Krishna Reddy; Li Niu; Dong Xing; Wenhao Hu

doi:10.1021/acs.orglett.9b01470

Cu(I)-Catalyzed Three-Component Reaction of α-Diazo Amide with Terminal Alkyne and Isatin Ketimine via Electrophilic Trapping of Active Alkynoate-Copper Intermediate

Jiuwei Che
, Alavala Gopi Krishna Reddy
, Li Niu
, Dong Xing^*
, Wenhao Hu

^*此作品的通讯作者

化学与分子工程学院

科研成果: 期刊稿件 › 文章 › 同行评审

21 引用（Scopus）

摘要

A three-component reaction between terminal alkyne, α-diazo amide, and isatin ketimine is realized by utilizing copper catalysis. A series of alkynyl-containing 3,3-disubstituted oxindoles were synthesized with high efficiency and diastereoselectivity under mild reaction conditions. This transformation is proposed to proceed through a Mannich-type trapping of an alkynoate copper intermediate derived from terminal alkyne and copper carbene species.

源语言	英语
页（从-至）	4571-4574
页数	4
期刊	Organic Letters
卷	21
期	12
DOI	https://doi.org/10.1021/acs.orglett.9b01470
出版状态	已出版 - 21 6月 2019

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title = "Cu(I)-Catalyzed Three-Component Reaction of α-Diazo Amide with Terminal Alkyne and Isatin Ketimine via Electrophilic Trapping of Active Alkynoate-Copper Intermediate",

abstract = "A three-component reaction between terminal alkyne, α-diazo amide, and isatin ketimine is realized by utilizing copper catalysis. A series of alkynyl-containing 3,3-disubstituted oxindoles were synthesized with high efficiency and diastereoselectivity under mild reaction conditions. This transformation is proposed to proceed through a Mannich-type trapping of an alkynoate copper intermediate derived from terminal alkyne and copper carbene species.",

author = "Jiuwei Che and Reddy, \{Alavala Gopi Krishna\} and Li Niu and Dong Xing and Wenhao Hu",

note = "Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

year = "2019",

month = jun,

day = "21",

doi = "10.1021/acs.orglett.9b01470",

language = "英语",

volume = "21",

pages = "4571--4574",

journal = "Organic Letters",

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publisher = "American Chemical Society",

number = "12",

}

TY - JOUR

T1 - Cu(I)-Catalyzed Three-Component Reaction of α-Diazo Amide with Terminal Alkyne and Isatin Ketimine via Electrophilic Trapping of Active Alkynoate-Copper Intermediate

AU - Che, Jiuwei

AU - Reddy, Alavala Gopi Krishna

AU - Niu, Li

AU - Xing, Dong

AU - Hu, Wenhao

PY - 2019/6/21

Y1 - 2019/6/21

N2 - A three-component reaction between terminal alkyne, α-diazo amide, and isatin ketimine is realized by utilizing copper catalysis. A series of alkynyl-containing 3,3-disubstituted oxindoles were synthesized with high efficiency and diastereoselectivity under mild reaction conditions. This transformation is proposed to proceed through a Mannich-type trapping of an alkynoate copper intermediate derived from terminal alkyne and copper carbene species.

AB - A three-component reaction between terminal alkyne, α-diazo amide, and isatin ketimine is realized by utilizing copper catalysis. A series of alkynyl-containing 3,3-disubstituted oxindoles were synthesized with high efficiency and diastereoselectivity under mild reaction conditions. This transformation is proposed to proceed through a Mannich-type trapping of an alkynoate copper intermediate derived from terminal alkyne and copper carbene species.

UR - https://www.scopus.com/pages/publications/85067669711

U2 - 10.1021/acs.orglett.9b01470

DO - 10.1021/acs.orglett.9b01470

M3 - 文章

C2 - 31184185

AN - SCOPUS:85067669711

SN - 1523-7060

VL - 21

SP - 4571

EP - 4574

JO - Organic Letters

JF - Organic Letters

IS - 12

ER -

Cu(I)-Catalyzed Three-Component Reaction of α-Diazo Amide with Terminal Alkyne and Isatin Ketimine via Electrophilic Trapping of Active Alkynoate-Copper Intermediate

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