实用助剂促进酮的高立体选择性β-C(sp3)-H 碘化反应。
Highly Versatile β-C(sp)-H Iodination of Ketones Using a Practical Auxiliary.
机构信息
Department of Chemistry, The Scripps Research Institute , 10550 N. Torrey Pines Road, La Jolla, California 92037, United States.
出版信息
J Am Chem Soc. 2017 Sep 13;139(36):12394-12397. doi: 10.1021/jacs.7b06851. Epub 2017 Aug 29.
Abstract
The first example of palladium(II)-catalyzed β-C(sp)-H iodination of a wide range of ketones using a commercially available aminooxyacetic acid auxiliary has been achieved. This L, X-type directing group overcomes the limitations of the transient directing group approach for C(sp)-H functionalization of ketones. Practical advantages of this method include simple installation of the auxiliary without chromatography, exceptional tolerance of α-functional groups, as well as alkenes and alkynes, and rapid access to diverse sterically hindered quaternary centers.
摘要
首例钯（II）催化的广泛酮类化合物的 β-C(sp)-H 碘代反应，使用了一种商业可得的氨氧乙酸助剂。这种 L、X 型导向基团克服了酮类化合物 C(sp)-H 官能化中瞬态导向基团方法的局限性。该方法的实际优点包括辅助剂的简单安装而无需进行色谱分离、对α-官能团的优异耐受性以及对烯烃和炔烃的耐受性，以及快速获得各种空间位阻的季碳原子。
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