Gold-catalyzed intramolecular aminoarylation of alkenes: C-C bond formation through bimolecular reductive elimination.

Gold-catalyzed intramolecular aminoarylation of alkenes: C-C bond formation through bimolecular reductive elimination.
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DOI:
10.1002/anie.201002739
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发表时间:
2010-07-26
影响因子:
16.6
通讯作者:
Toste, F. Dean
Toste, F. Dean
中科院分区:
化学1区
文献类型:
--
作者:
Brenzovich, William E., Jr.;Benitez, Diego;Lackner, Aaron D.;Shunatona, Hunter P.;Tkatchouk, Ekaterina;Goddard, William A., III;Toste, F. Dean

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到目前为止,均相金配合物作为亲碳π酸的用途已经得到了很好的证实,有许多报道称,在不饱和碳-碳键上加入亲核试剂引发了金催化的反应虽然原裂解是常见的,但已经开发了一些反应,其中产生的有机金中间体被截获。例如,亲核试剂已被用来拦截由π键反应产生的阳离子有机金中间体与此相反,涉及中性有机金中间体的反应会因碳金键与亲电试剂的反应而终止。虽然亲电试剂通常是质子,但金(I)催化的碳基亲电试剂的碳杂化官能化反应已经被报道过根据最近关于金催化氧化转化的报道,我们设想这些金(I)中间体的氧化类似物也可能对反应性亲核试剂敏感。
The utility of homogeneous gold complexes as carbophilic π–acids has been heretofore well established, with numerous reports of gold-catalyzed reactions initiated by addition of nucleophiles into unsaturated carbon-carbon bonds.[1] While protodeauration is common, several reactions have been developed in which the resulting organogold intermediate was intercepted. For example, nucleophilic reagents have been employed to intercept cationic organogold intermediates derived from reactions with π-bonds.[2] In contrast, reactions involving neutral organogold intermediates are terminated by reaction of the resulting carbon-gold bond with an electrophile. While the electrophile is often a proton, gold (I)-catalyzed carbohetero-functionalization reactions using carbon-based electrophiles have been reported.[3] On the basis of recent reports of gold-catalyzed oxidative transformations,[4] we envisioned that the oxidized analogues of these gold (I) intermediates might also be susceptible to reactive nucleophilic reagents.
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