Zinc-catalyzed synthesis of 2-alkenylfurans via cross-coupling of enynones and diazo compounds

被引:61
作者
Gonzalez, Jesus
Lopez, Luis A. [1 ]
Vicente, Ruben
机构
[1] Univ Oviedo, Dept Quim Organ & Inorgan, Oviedo 33007, Spain
关键词
TRIFLUOROMETHYLATED ALKENES; TERMINAL ALKYNES; SOLAR-CELLS; CYCLOPROPANATION; GENERATION; IRON; CYCLIZATION; ALCOHOLS; HALIDES; KETONES;
D O I
10.1039/c4cc03960b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Inexpensive, less-toxic ZnCl2 serves as the catalyst for selective cross-coupling of enynones and diazo compounds, an unprecedented reaction pathway for zinc carbenoids. A cascade sequence comprising formal cyclization/cross-coupling leads to a variety of 2-alkenylfurans.
引用
收藏
页码:8536 / 8538
页数:3
相关论文
共 44 条
[11]   Rise of the Zinc Age in Homogeneous Catalysis? [J].
Enthaler, Stephan .
ACS CATALYSIS, 2013, 3 (02) :150-158
[12]   A NOVEL ROUTE TO CYCLOPROPANES FROM OLEFINS [J].
FURUKAWA, J ;
KAWABATA, N ;
NISHIMURA, J .
TETRAHEDRON LETTERS, 1966, (28) :3353-+
[13]   CARBENOID DECOMPOSITION OF ARYLDIAZOMETHANES WITH LITHIUM AND ZINC HALIDES . A CONVENIENT METHOD FOR SYNTHESIS OF ARYLCYCLOPROPANES [J].
GOH, SH ;
CLOSS, LE ;
CLOSS, GL .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (01) :25-&
[14]   Zinc-Catalyzed Synthesis of Functionalized Furans and Triarylmethanes from Enynones and Alcohols or Azoles: Dual X-H Bond Activation by Zinc [J].
Gonzalez, Jesus ;
Gonzalez, Javier ;
Perez-Calleja, Carmela ;
Lopez, Luis A. ;
Vicente, Ruben .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (22) :5853-5857
[15]   In Situ Generation of Zinc Carbenoids from Diazo Compounds and Zinc Salts: Asymmetric Synthesis of 1,2,3-Substituted Cyclopropanes [J].
Goudreau, Sebastien R. ;
Charette, Andre B. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (43) :15633-+
[16]   Rhodium(II)-Catalyzed Cross-Coupling of Diazo Compounds [J].
Hansen, Jorn H. ;
Parr, Brendan T. ;
Pelphrey, Philip ;
Jin, Quihui ;
Autschbach, Jochen ;
Davies, Huw M. L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (11) :2544-2548
[17]   Biorelevant Metals in Sustainable Metal CatalysisA Survey [J].
Holzwarth, Michael S. ;
Plietker, Bernd .
CHEMCATCHEM, 2013, 5 (07) :1650-1679
[18]   Preferential carbene insertion into Ge-H vs. other heavier group 14 hydrides via samarium carbenoids [J].
Kondo, Hitoshi ;
Yamanoi, Yoshinori ;
Nishihara, Hiroshi .
CHEMICAL COMMUNICATIONS, 2011, 47 (23) :6671-6673
[19]   Stereoselective cyclopropanation reactions [J].
Lebel, H ;
Marcoux, JF ;
Molinaro, C ;
Charette, AB .
CHEMICAL REVIEWS, 2003, 103 (04) :977-1050
[20]   Improved Zinc-Catalyzed Simmons-Smith Reaction: Access to Various 1,2,3-Trisubstituted Cyclopropanes [J].
Levesque, Eric ;
Goudreau, Sebastien R. ;
Charette, Andre B. .
ORGANIC LETTERS, 2014, 16 (05) :1490-1493