Highly Regioselective Synthesis of Substituted Isoindolinones via Ruthenium-Catalyzed Alkyne Cyclotrimerizations.
Highly Regioselective Synthesis of Substituted Isoindolinones via Ruthenium-Catalyzed Alkyne Cyclotrimerizations.
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DOI：
10.1002/adsc.201300055
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发表时间：
2013-08-12
影响因子：
5.4
通讯作者：
Sheppard, Tom D.
中科院分区：
文献类型：
--
作者：
Foster, Robert W.;Tame, Christopher J.;Hailes, Helen C.;Sheppard, Tom D.
用氯化（环辛基）（五甲基环戊二烯基）钌[Cp*RuCl（cod）]催化单取代炔与酰胺键联二炔的区域选择性环化反应，合成了多取代异吲哚啉酮.值得注意的是，二炔上三甲基甲硅烷基的存在通常导致对炔环三聚的区域选择性的完全控制。环化反应在可持续的非氯化溶剂中进行得很好，并且耐潮湿。优化的条件是有效的，与各种范围的炔和二炔。7-甲硅烷基异吲哚啉酮产物可以被卤化、脱甲硅烷基化或开环以获得一系列有用的官能化产物。
(Cyclooctadiene)(pentamethylcyclopentadiene)ruthenium chloride [Cp*RuCl(cod)] has been used to catalyze the regioselective cyclization of amide-tethered diynes with monosubstituted alkynes to give polysubstituted isoindolinones. Notably, the presence of a trimethylsilyl group on the diyne generally led to complete control over the regioselectivity of the alkyne cyclotrimerization. The cyclization reaction worked well in a sustainable non-chlorinated solvent and was tolerant of moisture. The optimized conditions were effective with a diverse range of alkynes and diynes. The 7-silylisoindolinone products could be halogenated, protodesilylated or ring opened to access a range of usefully functionalized products.
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影响因子：
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