PALLADIUM-CATALYZED COUPLING OF ARYL TRIFLATES WITH ORGANOSTANNANES
PALLADIUM-CATALYZED COUPLING OF ARYL TRIFLATES WITH ORGANOSTANNANES
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DOI：
10.1021/ja00252a029
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发表时间：
1987-09-02
影响因子：
15
通讯作者：
STILLE, JK
中科院分区：
文献类型：
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作者：
ECHAVARREN, AM;STILLE, JK
三氟甲磺酸芳基酯与烷基、乙烯基、炔属和芳基锡试剂在氯化锂存在下的钯催化偶联反应在温和条件下以高产率发生。然而，烯丙基三烷基锡试剂偶联的产率较低，并且观察到烯丙基的非选择性转移。将芳基偶联反应应用于喹啉生物碱杜巴明的合成。芳基三氟甲磺酸酯与六甲基二锡的钯催化偶联得到芳基三甲基锡烷或均偶联产物，这取决于锡试剂的量。对溴苯基三氟甲磺酸酯可以通过不同的钯催化剂与乙烯基三丁基锡通过碳-卤键或碳-氧键进行选择性偶联，钯催化的有机亲电试剂与功能化有机锡烷的偶联反应是一种多用途的碳-碳键形成方法。1，2该反应具有一般碳-碳键构造方法的许多吸引人的特征：在温和的条件下产率高;几乎所有的官能团，包括醛，都是耐受的;反应对空间位阻相对不敏感;并且观察到钯催化剂的高转化率。此外，多种多样的官能化有机锡烷容易通过许多不同的反应类型获得。1，3多种有机亲电体进行交叉偶联
The palladium-catalyzed coupling reaction of aryl triflates with alkyl, vinyl, acetylenic, and aryl tin reagents in the presence of lithium chloride takes place in high yields under mild conditions. However, allyltrialkyltin reagents coupled in loweryields, and unselective transfer of the allyl group was observed. The aryl coupling reaction was applied to a synthesis of the quinolinealkaloid dubamine. The palladium-catalyzed coupling of aryl triflates with hexamethylditin gave aryltri-methylstannanes or homocoupled products depending on the amount of tin reagent. p-Bromophenyl triflate could be coupled selectively with vinyltributyltin through either the carbon-halogen or the carbon-oxygen bond by using different palladium catalysts.The palladium-catalyzed coupling of organic electrophiles with functionalized organostannanes has emerged as a versatile method for carbon-carbon bond formation. 1, 2 This reaction has many of the attractive features of a general carbon-carbon bond con-struction method: yields are high under mild conditions; virtually all functional groups, including aldehydes, are tolerated; the re-action is relatively insensitiveto steric hindrance; and high turnovers of the palladium catalyst are observed. Furthermore, a diverse array of functionalized organostannanes are readily available by a number of different reaction types. 1, 3 A variety of organic electrophiles undergo the cross-coupling