Metal-Free 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-Mediated Cross-Dehydrogenative-Coupling (CDC) of Benzylic C(sp3)-H Bonds and Vinylic C(sp2)-H Bonds: Efficient One-Pot Synthesis of 1H-Indenes

被引:41
作者
Wang, He [1 ]
Zhao, Yu-Long [1 ]
Li, Lei [1 ]
Li, Sha-Sha [1 ]
Liu, Qun [1 ]
机构
[1] NE Normal Univ, Dept Chem, Changchun 130024, Peoples R China
关键词
alkenes; benzylic compounds; C-C coupling; 2,3-dichloro-5,6-dicyanoquinone (DDQ); indenes; C-H ACTIVATION; DERIVATIVES; STRATEGY; MILD; FUNCTIONALIZATION; REARRANGEMENT; CONSTRUCTION; CYCLIZATION; COMPLEXES; ETHYLENE;
D O I
10.1002/adsc.201400357
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A novel 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-promoted intermolecular crossdehydrogenative coupling reaction of alkyl C(sp(3))-H bonds not adjacent to heteroatoms with vinylic C(sp(2))-H bonds has been developed. This new strategy provides a new, environmentally friendly, and efficient protocol for the synthesis of polysubstituted 1H-indenes in a single step via a radical-initiated two C(sp(2))-C(sp(2)) and C(sp(2))-C(sp(3)) bond formation process.
引用
收藏
页码:3157 / 3163
页数:7
相关论文
共 76 条
[1]   CDC Reactions of N-Aryl Tetrahydroisoquinolines Using Catalytic Amounts of DDQ: C-H Activation under Aerobic Conditions [J].
Alagiri, Kaliyamoorthy ;
Devadig, Pradeep ;
Prabhu, Kandikere R. .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (17) :5160-5164
[2]   Effect of the nature of metallocene complexes of group IV metals on their performance in catalytic ethylene and propylene polymerization [J].
Alt, HG ;
Köppl, A .
CHEMICAL REVIEWS, 2000, 100 (04) :1205-1221
[3]  
[Anonymous], 2014, Angew. Chem
[4]  
Antonchick A. P., 2013, ANGEW CHEM, V125, P3726
[5]  
Antonchick A. P., 2013, ANGEW CHEM INT EDIT, V52, P3638
[6]   Intermolecular oxidative cross-coupling of arenes [J].
Ashenhurst, James A. .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (02) :540-548
[7]   2,3-DICHLORO-5,6-DICYANO-1,4-BENZOQUINONE (DDQ) OXIDATION OF SILYL ENOL ETHERS TO ENONES VIA DDQ-SUBSTRATE ADDUCTS [J].
BHATTACHARYA, A ;
DIMICHELE, LM ;
DOLLING, UH ;
GRABOWSKI, EJJ ;
GRENDA, VJ .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (26) :6118-6120
[8]   DDQ-mediated Direct Intramolecular-Dehydrogenative-Coupling (IDC): Expeditious Approach to the Tetracyclic Core of Ergot Alkaloids [J].
Bhunia, Subhajit ;
Ghosh, Santanu ;
Dey, Dhananjay ;
Bisai, Alakesh .
ORGANIC LETTERS, 2013, 15 (10) :2426-2429
[9]   Indenyl complexes of Group 8 metals [J].
Cadierno, V ;
Diez, J ;
Gamasa, MP ;
Gimeno, J ;
Lastra, E .
COORDINATION CHEMISTRY REVIEWS, 1999, 193-5 :147-205
[10]   Direct sp3 C-H bond activation adjacent to nitrogen in heterocycles [J].
Campos, Kevin R. .
CHEMICAL SOCIETY REVIEWS, 2007, 36 (07) :1069-1084