Synthesis of Indenes via Bronsted Acid Catalyzed Cyclization of Diaryl- and Alkyl Aryl-1,3-dienes

被引:61
作者
Eom, Dahan [1 ]
Park, Sangjune [1 ]
Park, Youngchul [1 ]
Ryu, Taekyu [1 ]
Lee, Phil Ho [1 ]
机构
[1] Kangwon Natl Univ, Dept Chem, Chunchon 200701, South Korea
基金
新加坡国家研究基金会;
关键词
REGIOSELECTIVE SYNTHESIS; COUPLING REACTIONS; CONVENIENT SYNTHESIS; ASYMMETRIC-SYNTHESIS; INDANYL CATIONS; DERIVATIVES; CARBOCYCLIZATION; CARBOANNULATION; REARRANGEMENT; KETONES;
D O I
10.1021/ol302271w
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Substituted indenes can be synthesized via the Bronsted acid catalyzed cyclization of diaryl- and alkyl aryl-1,3-dienes. In this approach, treatment of symmetric or unsymmetric diaryl- and alkyl aryl-1,3-dienes with a catalytic amount of trifluoromethanesulfonic acid gives a variety of indene derivatives in good to excellent yields under mild conditions.
引用
收藏
页码:5392 / 5395
页数:4
相关论文
共 63 条
[1]   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
[2]   Highly regioselective synthesis of indene derivatives including an allene functional group via Pd/C-Catalyzed cyclization reaction in air [J].
Bi, Hai-Peng ;
Liu, Xue-Yuan ;
Gou, Fa-Rong ;
Guo, Li-Na ;
Duan, Xin-Hua ;
Liang, Yong-Min .
ORGANIC LETTERS, 2007, 9 (18) :3527-3529
[3]   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
[4]   Cobalt-catalyzed carbocyclization of o-Iodobenzaldehydes and o-Iodophenyl ketones with alkynes [J].
Chang, KJ ;
Rayabarapu, DK ;
Cheng, CH .
ORGANIC LETTERS, 2003, 5 (21) :3963-3966
[5]  
CHANG KJ, 2004, ORG LETT, V69, P4781, DOI DOI 10.1021/JO049506G
[6]   Differential response of estrogen receptor subtypes to 1,3-diarylindene and 2,3-diarylindene ligands [J].
Clegg, NJ ;
Paruthiyil, S ;
Leitman, DC ;
Scanlan, TS .
JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (19) :5989-6003
[7]   Nickel-catalyzed carboannulation reaction of o-bromobenzyl zinc bromide with unsaturated compounds [J].
Deng, Ruixue ;
Sun, Liangdong ;
Li, Zhi .
ORGANIC LETTERS, 2007, 9 (25) :5207-5210
[8]   CARBONIUM IONS .17. CYCLIZATIONS OF PENTADIENYY AND HEPTATRIENYL CATIONS [J].
DENO, NC ;
PITTMAN, CU ;
TURNER, JO .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (10) :2153-&
[9]   Comparative QSAR analysis of estrogen receptor ligands [J].
Gao, H ;
Katzenellenbogen, JA ;
Garg, R ;
Hansch, C .
CHEMICAL REVIEWS, 1999, 99 (03) :723-744
[10]   SYNTHESIS OF PERFLUOROALKYLATED INDENES [J].
GASSMAN, PG ;
RAY, JA ;
WENTHOLD, PG ;
MICKELSON, JW .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (17) :5143-5146