Synthesis of 9-alkylidene-9H-fluorenes by a novel, palladium-catalyzed cascade reaction of aryl halides and 1-aryl-1-alkynes

被引：71

作者：

Larock, RC ^{[1
]}

Tian, QP ^{[1
]}

机构：

[1] Iowa State Univ Sci & Technol, Dept Chem, Ames, IA 50011 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 22期

关键词：

D O I：

10.1021/jo010561o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the presence of a palladium catalyst and NaOAc, aryl iodides react with 1-aryl-1-alkynes to afford 9-alkylidene-9H-fluorenes in good yields. The products from this reaction are highly dependent on the base employed. This process appears to involve (1) oxidative addition of the aryL iodide to Pd(O), (2) alkyne insertion, (3) rearrangement of the resulting vinylic palladium intermediate to an arylpalladium species, and (4) aryl-aryl coupling with simultaneous regeneration of the Pd(O) catalyst. Consistent with this mechanism is the fact that 9-alkylidene-9H-fluorenes can also be prepared by the Pd-catalyzed rearrangement of 1,1-diaryl-2-iodo-1-alkenes.

引用

页码：7372 / 7379

页数：8

共 37 条

[1]

[Anonymous], 1996, PALLADIUM REAGENTS C

[2] THE PALLADIUM-CATALYZED REACTION OF ARYL IODIDES WITH MONOSUBSTITUTED AND DISUBSTITUTED ACETYLENES - A NEW SYNTHESIS OF TRISUBSTITUTED ALKENES [J].

CACCHI, S ;

FELICI, M ;

PIETRONI, B .

TETRAHEDRON LETTERS, 1984, 25 (29) :3137-3140

[3] DEVELOPMENT OF ORGANOPALLADIUM(IV) CHEMISTRY - FUNDAMENTAL-ASPECTS AND SYSTEMS FOR STUDIES OF MECHANISM IN ORGANOMETALLIC CHEMISTRY AND CATALYSIS [J].

CANTY, AJ .

ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (02) :83-90

[4] SOME PALLADIUM-CATALYZED CARBON CARBON BOND FORMATION REACTIONS [J].

CATELLANI, M ;

CHIUSOLI, GP ;

COSTA, M .

PURE AND APPLIED CHEMISTRY, 1990, 62 (04) :623-630

[5] A complex catalytic cycle leading to a regioselective synthesis of o,o'-disubstituted vinylarenes [J].

Catellani, M ;

Frignani, F ;

Rangoni, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (1-2) :119-122

[6] REACTION OF 1,1-DIARYL-2-HALOETHYLENES WITH BUTYLLITHIUM [J].

CURTIN, DY ;

FLYNN, EW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (17) :4714-4719

[7] TRANSITION-METAL-CATALYZED ANNELATION REACTIONS .5. PALLADIUM-CATALYZED C-H ACTIVATION OF TERT-BUTYL GROUPS - A SIMPLE SYNTHESIS OF 1,2-DIHYDROCYCLOBUTABENZENE DERIVATIVES [J].

DYKER, G .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (01) :103-105

[8] A palladium-catalyzed domino coupling process leading to annelated pentafulvenes [J].

Dyker, G ;

Nerenz, F ;

Siemsen, P ;

Bubenitschek, P ;

Jones, PG .

CHEMISCHE BERICHTE, 1996, 129 (10) :1265-1269

[9] TRANSITION-METAL-CATALYZED ANNULATION REACTIONS .7. PALLADIUM-CATALYZED C-H ACTIVATION AT METHOXY GROUPS - REGIOCHEMISTRY OF THE DOMINO COUPLING PROCESSES [J].

DYKER, G .

CHEMISCHE BERICHTE, 1994, 127 (04) :739-742

[10] Synthesis of polycyclic hydrocarbons by palladium-catalyzed cross-coupling reactions of vinylic bromides with diphenylacetylene [J].

Dyker, G ;

Siemsen, P ;

Sostmann, S ;

Wiegand, A ;

Dix, I ;

Jones, PG .

CHEMISCHE BERICHTE-RECUEIL, 1997, 130 (02) :261-265

← 1 2 3 4 →