Synthesis of a simplified version of stable bulky and rigid cyclic (alkyl)(amino)carbenes, and catalytic activity of the ensuing gold(I) complex in the three-component preparation of 1,2-dihydroquinoline derivatives.
Synthesis of a simplified version of stable bulky and rigid cyclic (alkyl)(amino)carbenes, and catalytic activity of the ensuing gold(I) complex in the three-component preparation of 1,2-dihydroquinoline derivatives.
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DOI：
10.1021/ja902051m
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发表时间：
2009-06-24
影响因子：
15
通讯作者：
Bertrand G
中科院分区：
文献类型：
--
作者：
Zeng X;Frey GD;Kinjo R;Donnadieu B;Bertrand G
作为合成稳定的螺环(烷基)(氨基)卡宾的前体，顺式和反式2，4-二甲基-3-环己烯甲醛(三联式)的混合物为95/5，其中2-甲基取代的环己烯基为后续金属提供空间保护。这种卡宾作为过渡金属催化剂配位体的效率首次通过金(I)催化的内炔与仲二烷基胺的氢胺化反应来说明，这一过程几乎没有先例。该反应的可行性大大扩大了1，2-二氢喹啉衍生物及其相关含氮杂环的一锅三组分合成的范围。事实上，使用了两种不同的炔烃，其中包括用于第一步的内部炔烃。
A 95/5 mixture of cis and trans 2,4-dimethyl-3-cyclohexenecarboxaldehyde (trivertal), a common fragrance and flavor material produced in bulk quantities, serves as the precursor for the synthesis of a stable spirocyclic (alkyl)(amino)carbene, in which the 2-methyl-substituted cyclohexenyl group provides steric protection to an ensuing metal. The efficiency of this carbene as ligand for transition metal based catalysts is first illustrated by the gold(I) catalyzed hydroamination of internal alkynes with secondary dialkyl amines, a process with little precedent. The feasibility of this reaction allows for significantly enlarging the scope of the one-pot three-component synthesis of 1,2-dihydroquinoline derivatives, and related nitrogen-containing heterocycles. Indeed, two different alkynes were used, which include an internal alkyne for the first step.
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影响因子：
2.8
作者：
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通讯作者：
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影响因子：
2.8
作者：
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影响因子：
4
作者：
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影响因子：
1.8
作者：
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通讯作者：
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影响因子：
7.3
作者：
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通讯作者：
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