Gold-Catalyzed Cascade Annulations of 2-(Ynol)aryl Aldehydes: Facile Synthesis of Benzochromanes and Benzobicyclo[n.3.1]acetals

被引：68
作者：
Liu, Le-Ping [1 ]
Hammond, Gerald B. [1 ]
机构：
[1] Univ Louisville, Dept Chem, Louisville, KY 40292 USA
来源：
ORGANIC LETTERS | 2010年 / 12卷 / 20期
基金：
美国国家科学基金会;
关键词：
ELECTROPHILIC CYCLIZATION; O-ALKYNYLBENZALDEHYDES; EFFICIENT SYNTHESIS; BENZANNULATION; HETEROCYCLES; COMPLEXES; INSERTION; ALKYNES; TANDEM; CYCLOADDITION;
D O I：
10.1021/ol101985d
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Gold-catalyzed reactions of 2-(ynol)aryl aldehydes were investigated. Benzochromanes were obtained from the reaction when AuCl3 was employed as the catalyst, whereas benzobicyclo[n 3.1]acetals were produced when triazole-gold was employed as the catalyst Plausible mechanisms are discussed.
引用
收藏
页码：4640 / 4643
页数：4
相关论文
共 44 条
[1]   Alternative synthetic methods through new developments in catalysis by gold [J].
Arcadi, Antonio .
CHEMICAL REVIEWS, 2008, 108 (08) :3266-3325
[2]   AuBr3-catalyzed [4+2] benzannulation between an enynal unit and enol [J].
Asao, N ;
Aikawa, H ;
Yamamoto, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (24) :7458-7459
[3]   Lewis acid-catalyzed benzannulation via unprecedented [4+2] cycloaddition of o-alkynyl(oxo)benzenes and enynals with alkynes [J].
Asao, N ;
Nogami, T ;
Lee, S ;
Yamamoto, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) :10921-10925
[4]   AuCl3-catalyzed benzannulation:: Synthesis of naphthyl ketone derivatives from o-alkynylbenzaldehydes with alkynes [J].
Asao, N ;
Takahashi, K ;
Lee, S ;
Kasahara, T ;
Yamamoto, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (43) :12650-12651
[5]   Gold- and copper-catalyzed [4+2] benzannulations between enynal or enynone units and 2π-systems [J].
Asao, Naoki .
SYNLETT, 2006, (11) :1645-1656
[6]   Cyclization of carbonyl groups onto alkynes upon reaction with IPy2BF4 and their trapping with nucleophiles:: A versatile trigger for assembling oxygen heterocycles [J].
Barluenga, J ;
Vázquez-Villa, H ;
Ballesteros, A ;
González, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (30) :9028-9029
[7]   PtII-catalyzed synthesis of 9-oxabicyclo-[3.3.1]nona-2,6-dienes from 2-alkynyl-1-carbonylbenzenes and allylsilanes by an allylation/annulation cascade [J].
Bhunia, Sabyasachi ;
Wang, Kuo-Chang ;
Liu, Rai-Shung .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (27) :5063-5066
[8]   1,2,3-Triazole as a Special "X-Factor" in Promoting Hashmi Phenol Synthesis [J].
Chen, Yunfeng ;
Yan, Wuming ;
Akhmedov, Novruz G. ;
Shi, Xiaodong .
ORGANIC LETTERS, 2010, 12 (02) :344-347
[9]   Carbo- and heterocyclisation of oxygen- and nitrogen-containing electrophiles by platinum, gold, silver and copper species [J].
Das, Arindam ;
Abu Sohel, Shariar Md. ;
Liu, Rai-Shung .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (05) :960-979
[10]   Triazole-Au(I) Complexes: A New Class of Catalysts with Improved Thermal Stability and Reactivity for Intermolecular Alkyne Hydroamination [J].
Duan, Haifeng ;
Sengupta, Sujata ;
Petersen, Jeffrey L. ;
Akhmedov, Novruz G. ;
Shi, Xiaodong .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (34) :12100-+
12345