Synthesis of 2-Indol-3-ylbenzofulvenes through a Tandem Reaction Catalyzed by Cationic Gold(I) Complexes

被引：14

作者：

Alvarez, Estela ^{[1
]}

Miguel, Delia ^{[1
]}

Garcia-Garcia, Patricia ^{[1
]}

Fernandez-Rodriguez, Manuel A. ^{[1
]}

Rodriguez, Felix ^{[2
]}

Sanz, Roberto ^{[1
]}

机构：

[1] Univ Burgos, Fac Ciencias, Dept Quim, Area Quim Organ, Burgos 09001, Spain

[2] Univ Oviedo, Inst Univ Quim Organomet Enrique Moles, E-33006 Oviedo, Spain

来源：

SYNTHESIS-STUTTGART | 2012年 / 44卷 / 12期

关键词：

benzofulvenes; catalysis; gold; indoles; tandem reactions; CYCLIZATION; CYCLOISOMERIZATION; BENZOFULVENES; POLYMER; LIGAND; CARBON;

D O I：

10.1055/s-0031-1290950

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new access to benzofulvenes bearing an indol-3-yl substituent at C-2 has been developed. Treatment of 3-propargylindoles possessing an additional hydroxy group at the other propargylic position with a cationic gold(I) complex triggers a tandem 1,2-indole migration/aura-iso-Nazarov cyclization/elimination sequence that takes place under mild conditions.

引用

页码：1874 / 1884

页数：11

共 44 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] Solvent- and ligand-induced switch of selectivity in gold(I)-catalyzed tandem reactions of 3-propargylindoles [J].

Alvarez, Estela ;

Miguel, Delia ;

Garcia-Garcia, Patricia ;

Fernandez-Rodriguez, Manuel A. ;

Rodriguez, Felix ;

Sanz, Roberto .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2011, 7 :786-793

[3] Concepts of nature in organic synthesis: Cascade catalysis and multistep conversions in concert [J].

Bruggink, A ;

Schoevaart, R ;

Kieboom, T .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2003, 7 (05) :622-640

[4] A Tandem Catalytic Approach to Methyleneindenes: Mechanistic Insights into gem-Dibromoolefin Reactivity [J].

Bryan, Christopher S. ;

Lautens, Mark .

ORGANIC LETTERS, 2010, 12 (12) :2754-2757

[5] Photochemical C2-C6 Cyclization of Enyne-Allenes: Detection of a Fulvene Triplet Diradical in the Laser Flash Photolysis [J].

Bucher, Goetz ;

Mahajan, Atul A. ;

Schmittel, Michael .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (22) :8815-8828

[6] Synthesis and characterization of a new benzofulvene polymer showing a thermoreversible polymerization behavior [J].

Cappelli, A ;

Mohr, GL ;

Anzini, M ;

Vomero, S ;

Donati, A ;

Casolaro, M ;

Mendichi, R ;

Giorgi, G ;

Makovec, F .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (24) :9473-9476

[7] Ruthenium-Catalyzed Regioselective Cyclization of Aromatic Ketones with Alkynes: An Efficient Route to Indenols and Benzofulvenes [J].

Chinnagolla, Ravi Kiran ;

Jeganmohan, Masilamani .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (02) :417-423

[8] 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

[9] Silver and Bronsted Acid Catalyzed Nazarov-Type Cyclizations To Generate Benzofulvenes [J].

Cordier, Pierre ;

Aubert, Corinne ;

Malacria, Max ;

Lacote, Emmanuel ;

Gandon, Vincent .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (46) :8757-8760

[10] Gold-Catalyzed Carbon-Heteroatom Bond-Forming Reactions [J].

Corma, A. ;

Leyva-Perez, A. ;

Sabater, Maria J. .

CHEMICAL REVIEWS, 2011, 111 (03) :1657-1712

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