Visible light mediated, metal-free carbene transfer reactions of diazoalkanes with propargylic alcohols

被引：82

作者：

He, Feifei ^{[1
]}

Koenigs, Rene M. ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany

来源：

CHEMICAL COMMUNICATIONS | 2019年 / 55卷 / 33期

关键词：

ENANTIOSELECTIVE CYCLOPROPENATION; CATALYZED CYCLOPROPENATION; DIAZOCARBONYL COMPOUNDS; ALPHA-DIAZOESTERS; DIAZO; REARRANGEMENT; DIRHODIUM(II); ALKYNES; YLIDES;

D O I：

10.1039/c9cc00927b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The development of efficient carbene transfer reactions under mild reaction conditions is very important to access small molecules for applications in organic synthesis and drug discovery. Herein, we describe the application of blue light in photochemical carbene transfer reactions of donor acceptor diazoalkanes under mild reaction conditions with propargylic alcohols, which provides - in contrast to conventional metal-catalyzed carbene transfer reactions - an access to cyclopropenes.

引用

页码：4881 / 4884

页数：4

共 66 条

[1] Synthesis of 1,3-diaryl-3-trifluoromethylcyclopropenes by transition-metal-free reaction of 2,2,2-trifluoroacetophenone tosylhydrazones with alkynes: the effect of the trifluoromethyl group [J].

Barroso, Raquel ;

Jimenez, Azucena ;

Carmen Perez-Aguilar, M. ;

Cabal, Maria-Paz ;

Valdes, Carlos .

CHEMICAL COMMUNICATIONS, 2016, 52 (18) :3677-3680

[2] Iron Catalysis in Organic Synthesis [J].

Bauer, Ingmar ;

Knoelker, Hans-Joachim .

CHEMICAL REVIEWS, 2015, 115 (09) :3170-3387

[3] Exploiting and engineering hemoproteins for abiological carbene and nitrene transfer reactions [J].

Brandenberg, Oliver F. ;

Fasan, Rudi ;

Arnold, Frances H. .

CURRENT OPINION IN BIOTECHNOLOGY, 2017, 47 :102-111

[4] Gold(I)-Catalyzed Asymmetric Cyclopropenation of Internal Alkynes [J].

Briones, John F. ;

Davies, Huw M. L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (29) :11916-11919

[5] Silver Triflate-Catalyzed Cyclopropenation of Internal Alkynes with Donor-/Acceptor-Substituted Diazo Compounds [J].

Briones, John F. ;

Davies, Huw M. L. .

ORGANIC LETTERS, 2011, 13 (15) :3984-3987

[6]

BRUNNER J, 1980, J BIOL CHEM, V255, P3313

[7] Developments in the Photochemistry of Diazo Compounds [J].

Candeias, Nuno R. ;

Afonso, Carlos A. M. .

CURRENT ORGANIC CHEMISTRY, 2009, 13 (07) :763-787

[8] Coordination responsive tellurium-containing multilayer film for controlled delivery [J].

Cao, Wei ;

Wang, Lu ;

Xu, Huaping .

CHEMICAL COMMUNICATIONS, 2015, 51 (25) :5520-5522

[9] Designing "Totem' C2-Symmetrical Iron Porphyrin Catalysts for Stereoselective Cyclopropanations [J].

Carminati, Daniela Maria ;

Intrieri, Daniela ;

Caselli, Alessandro ;

Le Gac, Stephane ;

Boitrel, Bernard ;

Toma, Lucio ;

Legnani, Laura ;

Gallo, Emma .

CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (38) :13599-13612

[10] Palladium-Catalyzed Divergent Reactions of a-Diazocarbonyl Compounds with Allylic Esters: Construction of Quaternary Carbon Centers [J].

Chen, Zi-Sheng ;

Duan, Xin-Hua ;

Zhou, Ping-Xin ;

Ali, Shaukat ;

Luo, Jian-Yi ;

Liang, Yong-Min .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (06) :1370-1374

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