Facile one-pot syntheses of bromoacetylenes from bulky trialkylsilyl acetylenes

被引：23

作者：

Lee, T

Kang, HR

Kim, S

Kim, S

机构：

[1] Seoul Natl Univ, Coll Pharm, Inst Nat Prod Res, Seoul 110460, South Korea

[2] Seoul Natl Univ, Coll Pharm, Seoul 151742, South Korea

来源：

TETRAHEDRON | 2006年 / 62卷 / 17期

关键词：

haloalkyne; trialkylsilyl acetylene; desilylative bromination; AgF;

D O I：

10.1016/j.tet.2006.02.016

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Because haloalkynes are versatile intermediates in synthetic chemistry, the development of new efficient methods for the conversion of 1-trialkylsilylacetylenes to haloacetylenes in situ remains desirable, especially when the corresponding terminal acetylenes are unstable. Using AgF and NBS, we have successfully transformed various 1-(trialkylsilyl)acetylenes, including bulky trialkylsilyl acetylenes. into bromoacetylenes in high yield. The reactions are chemoselective: triisopropylsilyl ethers were not deprotected under these conditions. (c) 2006 Elsevier Ltd. All rights reserved.

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页码：4081 / 4085

页数：5

相关论文

共 29 条

[1] Halogenation of terminal acetylenes by perhalogenoalkanes under phase transfer catalysis conditions [J].

Abele, E ;

Fleisher, M ;

Rubina, K ;

Abele, R ;

Lukevics, E .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2001, 165 (1-2) :121-126

[2] Mild and selective phase transfer catalysed bromination of terminal acetylenes using carbon tetrabromide as reagent [J].

Abele, E ;

Rubina, K ;

Abele, R ;

Gaukhman, A ;

Lukevics, E .

JOURNAL OF CHEMICAL RESEARCH, 1998, (09) :618-619

[3] First total synthesis of naturally occurring (-)-nitidon and its enantiomer [J].

Bellina, F ;

Carpita, A ;

Mannocci, L ;

Rossi, R .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (12) :2610-2619

[4]

Brandsma L, 1988, PREPARATIVE ACETYLEN

[5] Oligosaccharide analogues of polysaccharides .6. Orthogonal protecting activating groups in an improved binomial synthesis of 'acetyleno-oligosaccharides' [J].

Cai, CZ ;

Vasella, A .

HELVETICA CHIMICA ACTA, 1996, 79 (01) :255-268

[6] Silver(I)-catalysed protiodesilylation of 1-(trimethylsilyl)-1-alkynes [J].

Carpita, A ;

Mannocci, L ;

Rossi, R .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (09) :1859-1864

[7] A one-pot multicomponent coupling reaction for the stereocontrolled synthesis of (Z)-trisubstituted allylic alcohols [J].

Chen, YK ;

Walsh, PJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (12) :3702-3703

[8] Concise total synthesis of the aporphine alkaloid 7,7′-bisdehydro-O-methylisopiline by an InCl3 mediated cycloisomerization reaction [J].

Fürstner, A ;

Mamane, V .

CHEMICAL COMMUNICATIONS, 2003, (17) :2112-2113

[9] Highly enantioselective phenylacetylene additions to both aliphatic and aromatic aldehydes [J].

Gao, G ;

Moore, D ;

Xie, RG ;

Pu, L .

ORGANIC LETTERS, 2002, 4 (23) :4143-4146

[10] Total synthesis of (S)-(-)-(E)-15,16-dihydrominquartynoic acid:: A highly potent anticancer agent [J].

Gung, BW ;

Kumi, G .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (10) :3488-3492