Silver-catalyzed direct selenylation of terminal alkynes through C-H bond functionalization

被引：24

作者：

Xavier, Mauricio C. D. F. ^{[1
]}

Goldani, Bruna ^{[1
]}

Schumacher, Ricardo F. ^{[1
]}

Perin, Gelson ^{[1
]}

Schneider, Paulo Henrique ^{[2
]}

Alves, Diego ^{[1
]}

机构：

[1] Univ Fed Pelotas, UFPel, CCQFA, Lab Sintese Organ Limpa,LASOL, POB 354, BR-35496010 Pelotas, RS, Brazil

[2] Univ Fed Rio Grande do Sul, Inst Quim, UFRGS, Porto Alegre, RS, Brazil

来源：

MOLECULAR CATALYSIS | 2017年 / 427卷

关键词：

C-H Functionalization; Alkynes; Silver; Selenium; Catalysis; HIGHLY EFFICIENT; CHALCOGENIDES SELENIDES; CYCLOADDITION REACTIONS; SYNTHETIC ROUTE; ACTIVATION; TELLURIDES; DICHALCOGENIDES; CYCLIZATION; ACETYLENES; WATER;

D O I：

10.1016/j.molcata.2016.11.033

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：

We described herein the use of a silver catalyst in the selenylation of terminal alkynes by direct C-H functionalization. These reactions were performed under mild conditions, reacting a range of terminal alkynes with different diorganyl diselenides using AgNO3 (10 mol-%) as catalyst in CH2Cl2 at 25 degrees C under air atmosphere. This is an efficient and general cross-coupling reaction and was performed with alkynes and diorganyl diselenides bearing electron-withdrawing and electron-donating groups affording the corresponding selanylalkynes in good to excellent yields. (C) 2016 Published by Elsevier B.V.

引用

页码：73 / 79

页数：7

共 84 条

[41] C-H Activation for the Construction of C-B Bonds [J].

Mkhalid, Ibraheem A. I. ;

Barnard, Jonathan H. ;

Marder, Todd B. ;

Murphy, Jaclyn M. ;

Hartwig, John F. .

CHEMICAL REVIEWS, 2010, 110 (02) :890-931

[42] Cryptand-22 as an efficient ligand for the copper-catalyzed cross-coupling reaction of diorgano dichalcogenides with terminalalkynes leading to the synthesis of alkynyl chalcogenides [J].

Mohammadi, Elmira ;

Movassagh, Barahman .

TETRAHEDRON LETTERS, 2014, 55 (09) :1613-1615

[43] Catalytic enantioselective synthesis of α-aminooxy and α-hydroxy ketone using nitrosobenzene [J].

Momiyama, N ;

Yamamoto, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (20) :6038-6039

[44] A General and Highly Efficient Protocol for the Synthesis of Chalcogenoacetylenes by Copper(I)-Terpyridine Catalyst [J].

Movassagh, Barahman ;

Yousefi, Ali ;

Momeni, Badri Zaman ;

Heydari, Sepideh .

SYNLETT, 2014, 25 (10) :1385-1390

[45] A simple and effective approach to the synthesis of alkynyl selenides from terminal alkynes [J].

Movassagh, Barahman ;

Navidi, Mozhgan .

CHINESE CHEMICAL LETTERS, 2012, 23 (09) :1035-1038

[46]

Murai S., 1999, ACTIVATION UNREACTIV

[47] Asymmetric silver-catalyzed reactions [J].

Naodovic, Marina ;

Yamamoto, Hisashi .

CHEMICAL REVIEWS, 2008, 108 (08) :3132-3148

[48] Silver-Catalyzed Tandem Hydroazidation/Alkyne-Azide Cycloaddition of Diynes with TMS-N3: An Easy Access to 1,5-Fused 1,2,3-Triazole Frameworks [J].

Ning, Yongquan ;

Wu, Nannan ;

Yu, Haifeng ;

Liao, Peiqiu ;

Li, Xingqi ;

Bi, Xihe .

ORGANIC LETTERS, 2015, 17 (09) :2198-2201

[49]

Nogueira C. W., 2011, PATAIS CHEM FUNCTION

[50] Organoselenium and organotellurium compounds: Toxicology and pharmacology [J].

Nogueira, CW ;

Zeni, G ;

Rocha, JBT .

CHEMICAL REVIEWS, 2004, 104 (12) :6255-6285

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