Highly chemoselective coupling of allenylstannanes with organic iodides promoted by Pd(PPh3)4/LiCl:: an efficient method for the synthesis of substituted allenes

被引：52

作者：

Huang, CW ^{[1
]}

Shanmugasundaram, M ^{[1
]}

Chang, HM ^{[1
]}

Cheng, CH ^{[1
]}

机构：

[1] Tsing Hua Univ, Dept Chem, Hsinchu 300, Taiwan

来源：

TETRAHEDRON | 2003年 / 59卷 / 20期

关键词：

palladium and compounds; coupling reactions; lithium and compounds; allenes;

D O I：

10.1016/S0040-4020(03)00516-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient method for the preparation of various monosubstituted arylallenes, disubstituted allenes and alkenylallenes via palladium-catalyzed coupling of allenylstannanes with aryl iodides or alkenyl iodides is described. The coupling reaction was carried out in the presence of Pd(PPh3)(4) and LiCl using DMF as solvent. The possible role of LiCl in this coupling process is discussed based on the Sn-119 NMR studies. (C) 2003 Published by Elsevier Science Ltd.

引用

收藏

页码：3635 / 3641

页数：7

相关论文

共 55 条

[1] PALLADIUM-CATALYZED COUPLING OF STANNYL ALLENES WITH ARYL IODIDES [J].

AIDHEN, IS ;

BRASLAU, R .

SYNTHETIC COMMUNICATIONS, 1994, 24 (06) :789-797

[2] MECHANISTIC ASPECTS ON THE FORMATION OF CHIRAL ALLENES FROM PROPARGYLIC ETHERS AND ORGANOCOPPER REAGENTS [J].

ALEXAKIS, A ;

MAREK, I ;

MANGENEY, P ;

NORMANT, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (22) :8042-8047

[3] DIASTEREOSELECTIVE SYN OR ANTI OPENING OF PROPARGYLIC EPOXIDES - SYNTHESIS OF ALPHA-ALLENIC ALCOHOLS [J].

ALEXAKIS, A ;

MAREK, I ;

MANGENEY, P ;

NORMANT, JF .

TETRAHEDRON, 1991, 47 (09) :1677-1696

[4] Palladium-indium mediated Barbier-type allylation of aldehydes with allenes [J].

Anwar, U ;

Grigg, R ;

Rasparini, M ;

Savic, V ;

Sridharan, V .

CHEMICAL COMMUNICATIONS, 2000, (08) :645-646

[5] THE STILLE COUPLING REACTION OF ARYL TRIFLATES WITH N-TRIBUTYLALLENYL STANNANE - A GENERAL-ROUTE TO ARYLALLENES [J].

BADONE, D ;

CARDAMONE, R ;

GUZZI, U .

TETRAHEDRON LETTERS, 1994, 35 (30) :5477-5480

[6]

Brandsma L., 1981, Synthesis of Acetylenes, Allenes, Cumulenes: A Laboratory Manual

[7] Strategy for the preparation of allenes from alpha,beta-unsaturated and saturated ketones via enol phosphates [J].

Brummond, KM ;

Dingess, EA ;

Kent, JL .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (18) :6096-6097

[8] Highly regioselective and stereoselective allylation of aldehydes via palladium-catalyzed in situ hydrostannylation of allenes [J].

Chang, HM ;

Cheng, CH .

ORGANIC LETTERS, 2000, 2 (22) :3439-3442

[9] CARBOPALLADATION OF FUNCTIONALIZED ALLENES - REGIOSELECTIVITY OF THE REACTION OF CARBONUCLEOPHILES WITH THE INTERMEDIATE PI-ALLYL PALLADIUM COMPLEXES [J].

CHAPTAL, N ;

COLOVRAYGOTTELAND, V ;

GRANDJEAN, C ;

CAZES, B ;

GORE, J .

TETRAHEDRON LETTERS, 1991, 32 (15) :1795-1798

[10]

COLQUHOUN HM, 1988, NEW PATHWAYS ORGANIC

← 1 2 3 4 5 6 →