Cross-coupling reactions of aromatic and heteroaromatic silanolates with aromatic and heteroaromatic halides.
Cross-coupling reactions of aromatic and heteroaromatic silanolates with aromatic and heteroaromatic halides.
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DOI：
10.1021/ja8091449
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发表时间：
2009-03-04
影响因子：
15
通讯作者：
Muhuhi JM
中科院分区：
文献类型：
--
作者：
Denmark SE;Smith RC;Chang WT;Muhuhi JM
大量芳基和杂芳基硅烷醇的碱金属盐（钾和钠）在温和条件下与广泛的芳香族溴化物和氯化物进行有效的交叉偶联以形成多取代联芳基。这些偶联反应成功的关键特征及其相当大的范围是使用双（三叔丁基膦）钯。在优化的条件下，富电子，贫电子，和空间位阻的芳基硅烷醇酯提供良好的产率的交叉偶联产物。许多官能团与偶联条件相容，例如酯、酮、缩醛、醚、甲硅烷基醚和二甲氨基。两种特别具有挑战性的底物，（2-苯并呋喃基）二甲基硅烷醇盐和（2，6-二氯苯基）二甲基硅烷醇盐，作为其钠盐制备，在偶联反应中显示出优异的活性，在前一种情况下，也与芳香族氯化物。还描述了用于有效合成宽范围的芳香族硅烷醇的一般方法。
The alkali-metal salts (potassium and sodium) of a large number of aryl- and heteroarylsilanols undergo efficient cross coupling with a wide range of aromatic bromides and chlorides under mild conditions to form polysubstituted biaryls. The critical feature for the success of these coupling reactions and their considerable scope is the use of bis(tri-tert-butylphosphine)palladium. Under the optimized conditions, electron-rich, electron-poor, and sterically hindered arylsilanolates afford cross-coupling products in good yields. Many functional groups are compatible with the coupling conditions such as esters, ketones, acetals, ethers, silyl ethers, and dimethylamino groups. Two particularly challenging substrates, (2-benzofuranyl)dimethylsilanolate and (2,6-dichlorophenyl)dimethylsilanolate prepared as their sodium salts showed excellent activity in the coupling reactions, in the former case also with aromatic chlorides. General methods for the efficient synthesis of a wide range of aromatic silanols are also described.
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影响因子：
15
作者：
Denmark, Scott E.;Butler, Christopher R.
通讯作者：
Butler, Christopher R.
影响因子：
2
作者：
Denmark, Scott E.;Smith, Russell C.
通讯作者：
Smith, Russell C.
影响因子：
5.2
作者：
Denmark, SE;Baird, JD
通讯作者：
Baird, JD
影响因子：
15
作者：
Denmark, SE;Sweis, RF
通讯作者：
Sweis, RF
影响因子：
15
作者：
Dai, CY;Fu, GC
通讯作者：
Fu, GC