Synthesis of isochromenones and oxepines via Pd-catalyzed cascade cyclization of alkynes and benzynes involving C-H activation

被引:32
作者
Parthasarathy, Kanniyappan [1 ]
Han, Han [1 ]
Prakash, Chandran [1 ]
Cheng, Chien-Hong [1 ]
机构
[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu 30013, Taiwan
关键词
HIGHLY EFFICIENT ROUTE; FUSED POLYCYCLIC AROMATICS; REGIOSELECTIVE SYNTHESIS; ARYL HALIDES; 2+2+2 CYCLOADDITION; BICYCLIC ALKENES; TERMINAL ALKYNES; FACILE SYNTHESIS; BOND ACTIVATION; PALLADIUM;
D O I
10.1039/c2cc31807e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new method for the synthesis of various isochromen-6-ones and phenanthro[1,10-bc]oxepines via a palladium-catalyzed cascade carbocyclization of 2-iodobenzyl-3-phenylpropiolates and 1-iodo-2-(2-(phenylethynyl) benzyloxy) benzenes with arynes is described. The reactions involve interesting biscarbocyclization of alkynes and benzynes and C-H bond activation.
引用
收藏
页码:6580 / 6582
页数:3
相关论文
共 69 条
[11]   Regioselective [2+2+2] cycloaddition of a nickel-benzyne complex with 1,3-diynes [J].
Deaton, KR ;
Gin, MS .
ORGANIC LETTERS, 2003, 5 (14) :2477-2480
[12]   Organometallic generation and capture of ortho-arynes [J].
Dyke, Alan M. ;
Hester, Alison J. ;
Lloyd-Jones, Guy C. .
SYNTHESIS-STUTTGART, 2006, (24) :4093-4112
[13]   PALLADIUM-CATALYZED C-H ACTIVATION OF METHOXY GROUPS - A FACILE SYNTHESIS OF SUBSTITUTED 6H-DIBENZO[B,D]PYRANS [J].
DYKER, G .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1992, 31 (08) :1023-1025
[14]   A new reaction sequence involving palladium-catalyzed unsymmetrical aryl coupling [J].
Faccini, F ;
Motti, E ;
Catellani, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (01) :78-79
[15]   Synthesis of Phenanthrone Derivatives from sec-Alkyl Aryl Ketones and Aryl Halides via a Palladium-Catalyzed Dual C-H Bond Activation and Enolate Cyclization [J].
Gandeepan, Parthasarathy ;
Parthasarathy, Kanniyappan ;
Cheng, Chien-Hong .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (25) :8569-+
[16]   SUPPRESSION OF ALKENE ISOMERIZATION IN PRODUCTS FROM INTRAMOLECULAR HECK REACTIONS BY ADDITION OF TL(I) SALTS [J].
GRIGG, R ;
LOGANATHAN, V ;
SANTHAKUMAR, V ;
SRIDHARAN, V ;
TEASDALE, A .
TETRAHEDRON LETTERS, 1991, 32 (05) :687-690
[17]   Palladium catalysed cascade alkyne-arene vinylation/alkylation approach to polyfused heterocycles. [J].
Grigg, R ;
Loganathan, V ;
Sridharan, V .
TETRAHEDRON LETTERS, 1996, 37 (19) :3399-3402
[18]   PALLADIUM-CATALYZED SYNTHESIS OF SPIROINDOLINES [J].
GRIGG, R ;
FRETWELL, P ;
MEERHOLTZ, C ;
SRIDHARAN, V .
TETRAHEDRON, 1994, 50 (02) :359-370
[19]   Biaryl synthesis via palladium-catalyzed aryne multicomponent coupling [J].
Henderson, Jaclyn L. ;
Edwards, Andrew S. ;
Greaney, Michael F. .
ORGANIC LETTERS, 2007, 9 (26) :5589-5592
[20]   Three-component coupling of benzyne: Domino intermolecular carbopalladation [J].
Henderson, Jaclyn L. ;
Edwards, Andrew S. ;
Greaney, Michael F. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (23) :7426-7427