Silane-promoted cycloisomerization of functionalized 1,6-dienes catalyzed by a cationic (π-allyl)palladium complex

被引：35

作者：

Widenhoefer, RA ^{[1
]}

Perch, NS ^{[1
]}

机构：

[1] Duke Univ, Paul M Gross Chem Lab, Durham, NC 27708 USA

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 07期

关键词：

D O I：

10.1021/ol9908981

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A 1:1 mixture of the (pi-allyl)palladium complex (eta(3)-C3H5)Pd(Cl)PCy3 and NaB[3,5-C6H3(CF3)(2)](4) in the presence of HSiEt3 catalyzed the cycloisomerization of functionalized 1,6-dienes to form 1,2-disubstituted cyclopentenes in good yield with high selectivity (typically >94%). The protocol tolerated a range of functional groups and substitution at one of the allylic carbon atoms.

引用

页码：1103 / 1105

页数：3

共 23 条

[1] MECHANISM OF A COBALT(III)-CATALYZED OLEFIN HYDROSILATION REACTION - DIRECT EVIDENCE FOR A SILYL MIGRATION PATHWAY [J].

BROOKHART, M ;

GRANT, BE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (06) :2151-2156

[2] POLYMERS WITH MAIN-CHAIN CHIRALITY - SYNTHESIS OF HIGHLY ISOTACTIC, OPTICALLY-ACTIVE POLY(4-TERT-BUTYLSTYRENE-ALT-CO) USING PD(II) CATALYSTS BASED ON C-2-SYMMETRICAL BISOXAZOLINE LIGANDS [J].

BROOKHART, M ;

WAGNER, MI ;

BALAVOINE, GGA ;

HADDOU, HA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (08) :3641-3642

[3] FACILE INTERMOLECULAR ACTIVATION OF C-H BONDS IN METHANE AND OTHER HYDROCARBONS AND SI-H BONDS IN SILANES WITH THE IR(III) COMPLEX CP-ASTERISK-(PME3)IR(CH3)(OTF) [J].

BURGER, P ;

BERGMAN, RG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) :10462-10463

[4] HIGHLY SELECTIVE SKELETAL REORGANIZATION OF 1,6-ENYNE AND 1,7-ENYNE TO 1-VINYLCYCLOALKENES CATALYZED BY [RUCL2(CO)(3)](2) [J].

CHATANI, N ;

MORIMOTO, T ;

MUTO, T ;

MURAI, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (13) :6049-6050

[5] Catalytic dimerization reactions of alpha-olefins and alpha,omega-dienes with Cp(2)ZrCl(2)/poly(methylalumoxane): Formation of dimers, carbocycles, and oligomers [J].

Christoffers, J ;

Bergman, RG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (19) :4715-4716

[6] Mechanistic studies of catalytic olefin dimerization reactions using electrophilic eta(3)-allyl-palladium(II) complexes [J].

DiRenzo, GM ;

White, PS ;

Brookhart, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (26) :6225-6234

[7] Mechanistic studies of palladium(II)-catalyzed hydrosilation and dehydrogenative silation reactions [J].

LaPointe, AM ;

Rix, FC ;

Brookhart, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (05) :906-917

[8] Silylation of styrene with vinylsilanes catalyzed by RuCl(SiR3)(CO)(PPh3)(2) and RuHCl(CO)(PPh3)(3) [J].

Marciniec, B ;

Pietraszuk, C .

ORGANOMETALLICS, 1997, 16 (20) :4320-4326

[9] Intramolecular cyclizations of enynes using RuClH(CO)(PPh3)3 [J].

Nishida, M ;

Adachi, N ;

Onozuka, K ;

Matsumura, H ;

Mori, M .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (25) :9158-9159

[10] Asymmetric cyclization/hydrosilylation of functionalized 1,6-dienes catalyzed by enantiomerically pure palladium pyridine-oxazoline complexes [J].

Perch, NS ;

Widenhoefer, RA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (29) :6960-6961

← 1 2 3 →