Synthesis of 4-alkyl-3-bromo-2(5H)-furanones and unsymmetrically disubstituted 3,4-dialkyl-2(5H)-furanones by palladium-catalyzed cross-coupling reactions
Synthesis of 4-alkyl-3-bromo-2(5H)-furanones and unsymmetrically disubstituted 3,4-dialkyl-2(5H)-furanones by palladium-catalyzed cross-coupling reactions
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DOI：
10.1016/s0040-4039(01)00609-8
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发表时间：
2001-06-04
影响因子：
1.8
通讯作者：
Rossi, R
中科院分区：
文献类型：
--
作者：
Bellina, F;Anselmi, C;Rossi, R
易得的3，4-二溴-2(5H)-呋喃酮在PdCl2(MeCN)(2)和AsPh3的催化下与烷基硼酸发生区域选择性交叉偶联反应，并以较大摩尔过量的Ag2O生成相应的4-烷基-3-溴-2(5H)-呋喃酮。这些单溴衍生物已被证明是不对称取代的3，3-二烷基-2(5H)-呋喃酮的有用前体，这些呋喃酮包括天然存在的外消旋形式的seiridin。(C)2001爱思唯尔科学有限公司。保留所有权利。
Easily available 3,4-dibromo-2(5H)-furanone undergoes a regioselective cross-coupling reaction with alkylboronic acids in the presence of catalytic amounts of PdCl2( MeCN)(2) and AsPh3 and a large molal excess of Ag2O to provide the corresponding 4-alkyl-3-bromo-2(5H)-furanones in satisfactory yields. These monobromo derivatives have proven to be useful precursors to unsymmetrically substituted 3,3-dialkyl-2(5H)-furanones which include the racemic form of naturally occurring seiridin. (C) 2001 Elsevier Science Ltd. All rights reserved.