An Efficient Protocol for the Stereoselective Construction of Multisubstituted Fluorine-Containing Alkenes. A Palladium-Catalyzed Bisstannylation of Fluorinated Internal Alkynes

被引：31

作者：

Konno, Tsutomu ^{[1
]}

Kinugawa, Ryoko ^{[1
]}

Morigaki, Atsunori ^{[1
]}

Ishihara, Takashi ^{[1
]}

机构：

[1] Kyoto Inst Technol, Dept Chem & Mat Technol, Sakyo Ku, Kyoto 6068585, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 21期

关键词：

ACETYLENE DERIVATIVES; VINYLPHOSPHONATES; CONVENIENT; FACILE; HEXAALKYLDITINS; ALLYLSTANNANES; REARRANGEMENT; ACCESS;

D O I：

10.1021/jo9017028

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

On treatment of various fluorinated internal alkynes with 1.2 equiv of hexabutylditin under the influence of 2.5 mol % of Pd(t-BuNC)(2)Cl(2) in THF at room temperature for 4 h, the bisstannylation proceeded smoothly to afford the corresponding bisstannylaled cis-adducts in high yields. Thus obtained adducts were subjected to the Stille cross-coupling reaction to give the corresponding tetrasubstituted fluorine-containing alkenes with defined stereochemistry in good yields.

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页码：8456 / 8459

页数：4

相关论文

共 24 条

[1] REGIOCONTROLLED AND STEREOCONTROLLED STANNYLMETALLATION OF 3,3-DIETHOXY-PROP-1-YNE AND 4,4-DIETHOXY-BUT-1-YNE - AN EFFICIENT ACCESS TO THE CORRESPONDING VINYLTINS WITH FIXED CONFIGURATIONS [J].

BEAUDET, I ;

PARRAIN, JL ;

QUINTARD, JP .

TETRAHEDRON LETTERS, 1991, 32 (44) :6333-6336

[2] Element-element addition to alkynes catalyzed by the group 10 metals [J].

Beletskaya, I ;

Moberg, C .

CHEMICAL REVIEWS, 1999, 99 (12) :3435-3461

[3] Preparation and reactions of 3,4-bisstannyl-2(5H)furanones [J].

Carter, NB ;

Mabon, R ;

Richecoeur, AME ;

Sweeney, JB .

TETRAHEDRON, 2002, 58 (44) :9117-9129

[4]

CASSON S, 1994, SYNTHESIS-STUTTGART, P1301

[5] A CONVENIENT STEREOSELECTIVE SYNTHESIS OF DISUBSTITUTED ALK-1-ENYL PHOSPHONATES [J].

CRISTAU, HJ ;

GASC, MB ;

MBIANDA, XY .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1994, 474 (1-2) :C14-C15

[6] Facile and stereoselective synthesis of vinylphosphonates [J].

Cristau, HJ ;

Mbianda, XY ;

Beziat, Y ;

Gasc, MB .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1997, 529 (1-2) :301-311

[7] Unexpected rearrangement of diethyl (±)(S,S)-1,2-epoxy-2-phenylpentylphosphonate by NH3(aqu):: An easy entry to ethyl 1-formyl-1-phenylbutylphosphonate [J].

Drag, M ;

Kafarski, P ;

Pirat, JL ;

Cristau, HJ .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2002, 177 (05) :1153-1156

[8] ON THE NATURE OF THE COPPER EFFECT IN THE STILLE CROSS-COUPLING [J].

FARINA, V ;

KAPADIA, S ;

KRISHNAN, B ;

WANG, CJ ;

LIEBESKIND, LS .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (20) :5905-5911

[9] The palladium catalyzed hydrostannation of 1-alkenylphosphonates:: A new approach to stereodefined α,β-disubstituted vinylphosphonates [J].

Huang, X ;

Xiong, ZC .

SYNTHETIC COMMUNICATIONS, 2003, 33 (14) :2511-2517

[10] Highly regio- and stereoselective carbostannylation reaction of fluorine-containing internal acetylenes with allylstannanes [J].

Konno, T ;

Takehana, T ;

Chae, J ;

Ishihara, T ;

Yamanaka, H .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (06) :2188-2190