Synthesis of 1,1-Disubstituted Allenylic Silyl Ethers Through Iron-Catalyzed Regioselective C(sp2)─H Functionalization of Allenes.
Synthesis of 1,1-Disubstituted Allenylic Silyl Ethers Through Iron-Catalyzed Regioselective C(sp2)─H Functionalization of Allenes.
复制标题
通过铁催化的二烯区域选择性 C(sp2)·H 官能化合成 1,1-二取代的烯基甲硅烷基醚。
DOI：
10.1055/a-2004-0951
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发表时间：
2023
期刊：
影响因子：
--
通讯作者：
Wang,Yi-Ming
中科院分区：
文献类型：
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作者：
Ding,Ruiqi;Wang,Yidong;Wang,Yi-Ming
我们报道了一种通过铁催化的单取代烷基联烯的C（sp2）-H键的功能化合成烯基硅醚的方法。在环戊二烯基铁二羰基催化剂和三异丙基甲硅烷基三氟甲磺酸酯作为硅烷化试剂的存在下，各种芳基醛是该转化中合适的偶联伙伴，以中等至优异的产率提供作为单一区域异构体的1，1-二取代烯基三异丙基甲硅烷基醚作为产物的集合。双三氟甲磺酰亚胺锂被确定为该转化中的关键添加剂。优化的方案是可扩展的，并且产物易于进一步转化以得到许多不饱和的多官能衍生物。
We report a synthesis of allenylic silyl ethers through iron-catalyzed functionalization of the C(sp2)–H bonds of monosubstituted alkylallenes. In the presence of a cyclopentadienyliron dicarbonyl based catalyst and triisopropylsilyl triflate as a silylation agent, a variety of aryl aldehydes were suitable coupling partners in this transformation, furnishing a collection of 1,1-disubstituted allenylic triisopropylsilyl ethers as products in moderate to excellent yields as a single regioisomer. Lithium bistriflimide was identified as a critical additive in this transformation. The optimized protocol was scalable, and the products were amenable to further transformation to give a number of unsaturated, polyfunctional derivatives.