Gold-Catalyzed Deacylative Cycloisomerization Reactions of 3-Acylindole/ynes: A New Approach for Carbazole Synthesis

被引:64
作者
Wang, Lu [1 ]
Li, Guijie [1 ]
Liu, Yuanhong [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
INTERMOLECULAR REACTIONS; INDOLES; ACTIVATION; ALKYNES; FRAGMENTATION; CONSTRUCTION; DERIVATIVES; PLATINUM;
D O I
10.1021/ol2012154
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of functionalized carbazoles through gold-catalyzed deacylative cycloisomerization of 3-acylindole/ynes is described. A mechanistic proposal for these transformations involving a novel carbonyl group facilitated heterolytic fragmentation upon the loss of an acylium ion intermediate is presented. The eliminated acylium ion species could be trapped by the organogold intermediate to afford acylcarbazoles.
引用
收藏
页码:3786 / 3789
页数:4
相关论文
共 61 条
[31]   Gold-Catalyzed Intramolecular Indole/Alkyne Cyclization Cascades through a Heterolytic Fragmentation: 1,5-Indole Migration and Allenylation [J].
Li, Guijie ;
Liu, Yuanhong .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (10) :3526-3528
[32]   Platinum-catalyzed formation of cyclic-ketone-fused indoles from N-(2-alkynylphenyl)lactams [J].
Li, Guotao ;
Huang, Xiaogen ;
Zhang, Liming .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (02) :346-349
[33]   Gold-catalyzed organic transformations [J].
Li, Zigang ;
Brouwer, Chad ;
He, Chuan .
CHEMICAL REVIEWS, 2008, 108 (08) :3239-3265
[34]   Intramolecular Pd(II)-catalyzed oxidative biaryl synthesis under air:: Reaction development and scope [J].
Liegault, Benoit ;
Lee, Doris ;
Huestis, Malcolm P. ;
Stuart, David R. ;
Fagnou, Keith .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (13) :5022-5028
[35]   Introduction: Coinage metals in organic synthesis [J].
Lipshutz, Bruce H. ;
Yamamoto, Yoshinori .
CHEMICAL REVIEWS, 2008, 108 (08) :2793-2795
[36]   Gold(I)-Catalyzed Tandem Cyclization Approach to Tetracyclic Indolines [J].
Liu, Yongxiang ;
Xu, Wenqing ;
Wang, Xiang .
ORGANIC LETTERS, 2010, 12 (07) :1448-1451
[37]   Synthesis of carbazoles and dibenzofurans via cross-coupling of o-iodoanilines and o-iodophenols with silylaryl triflates [J].
Liu, ZJ ;
Larock, RC .
ORGANIC LETTERS, 2004, 6 (21) :3739-3741
[38]   Gold-Catalyzed Intermolecular Reactions of (Z)-Enynols with Indoles for the Construction of Dihydrocyclohepta[b]indole Skeletons through a Cascade Friedel-Crafts/Hydroarylation Sequence [J].
Lu, Yuhua ;
Du, Xiangwei ;
Jia, Xueshun ;
Liu, Yuanhong .
ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (10) :1517-1522
[39]   Siamenol, a new carbazole alkaloid from Murraya siamensis [J].
Meragelman, KM ;
McKee, TC ;
Boyd, MR .
JOURNAL OF NATURAL PRODUCTS, 2000, 63 (03) :427-428
[40]   Sequenced reactions with Samarium(II) iodide.: Sequential intramolecular Barbier cyclization/Grob fragmentation for the synthesis of medium-sized carbocycles [J].
Molander, GA ;
Le Huérou, Y ;
Brown, GA .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (13) :4511-4516