Pd/Cu-Catalyzed Cross-Coupling of Bis(2-bromovinyl) Selenides with Terminal Acetylenes: Unusual Involvement of Selanyl Function in the Sonogashira Reaction

被引：0

作者：

Martynov, Alexander V. ^{[1
]}

Makhaeva, Nataliya A. ^{[1
]}

Musalov, Maxim V. ^{[1
]}

Albanov, Alexander I. ^{[1
]}

Amosova, Svetlana V. ^{[1
]}

机构：

[1] Russian Acad Sci, A E Favorsky Irkutsk Inst Chem, Siberian Div, 1 Favorsky Str, Irkutsk 664033, Russia

来源：

CATALYSTS | 2022年 / 12卷 / 12期

关键词：

2-bromovinyl selenides; cross-coupling; palladium catalyst; terminal acetylenes; endiynes; bis-(enynyl) selenides; STEREOSELECTIVE-SYNTHESIS; STEREOSPECIFIC SYNTHESIS; VINYLIC TELLURIDES; SE-77; NMR; CHALCOGENIDES; ALKYNES; ENYNES;

D O I：

10.3390/catal12121589

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The Pd/Cu-catalyzed Sonogashira reaction of (E,E)-bis(2-bromovinyl) selenide and (E,E)-bis(1-bromo-1-hexen-2-yl) selenide with terminal alkynes was found to proceed at room temperature involving both bromine atoms and the selanyl function. As a result, new bis-(1,3-enynyl) selenides and enediyne hydrocarbons are formed with a complete retention of the stereoconfiguration of the initial selenides. Due to steric hindrances in the cross-coupling at the selenyl function in the case of (E,E)-bis(1-bromo-1-hexen-2-yl) selenide, the second process is realized to a lesser extent than with unsubstituted (E,E)-bis(2-bromovinyl) selenide.

引用

页数：12

共 22 条

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A. V. Martynov
N. A. Makhaeva
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S. V. Amosova
Russian Journal of Organic Chemistry, 2021, 57 : 1882 - 1886
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[3] Cross Coupling of Bis[(E)-2-bromovinyl)] Selenide with Terminal Acetylenes in the Presence of Pd(PPh3)4: the First Example of the Sonogashira Cross Coupling Involving Vinyl Selenide
Martynov, A. V.
Makhaeva, N. A.
Musalov, M. V.
Amosova, S. V.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 57 (11) : 1882 - 1886
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[5] Cu(OAc)2 catalyzed Sonogashira cross-coupling reaction in amines
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EUROPEAN POLYMER JOURNAL, 2023, 196
[8] Pd(OAc)2 Catalyzed Sonogashira Cross-Coupling Reaction under Ultrasound Irradiation
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[9] Pd/Cu-Catalyzed Synthesis of Internal and Sila-Ynones by Direct Selective Acyl Sonogashira Cross-Coupling of Carboxylic Acids with Terminal Alkynes
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[10] Bimetallic Pd/Cu-Catalyzed Sonogashira Coupling-Elimination Reaction: An Efficient Synthesis of 2-Unsubstituted Terminal 1, 3-Enynes
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ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 12 (06)

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