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瞬态导向基团促进钯催化的苯甲醛和苄胺的C-H氧化反应。

Transient directing group enabled Pd-catalyzed C-H oxygenation of benzaldehydes and benzylic amines.

作者信息

Tian Mixiang, Shao Lidong, Su Xiaosan, Zhou Xuhong, Zhang Honglei, Wei Kun, Sun Ruifen, Wang Junliang

机构信息

Center for Scientific Research, Yunnan University of Chinese Medicine Kunming Yunnan 650500 P. R. China

School of Chemical Science and Technology, Yunnan University Kunming Yunnan 650500 P. R. China.

出版信息

RSC Adv. 2022 Jun 27;12(29):18722-18727. doi: 10.1039/d2ra00241h. eCollection 2022 Jun 22.

DOI:10.1039/d2ra00241h
PMID:35873337
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9235058/
Abstract

We report a general protocol for -C-H fluoroalkoxylation of benzaldehydes and benzylic amines utilizing an inexpensive amino amide as a transient directing group. In the presence of an electrophilic fluorinating bystanding oxidant and fluorinated alcohols, a wide range of benzaldehydes and benzylic amines could be oxygenated selectively at the ortho positions to afford fluoroalkyl aryl ethers. This elegant approach would provide appealing strategies for synthesis of drug molecules and natural products.

摘要

我们报道了一种通用的方案，该方案利用廉价的氨基酰胺作为瞬态导向基团，实现苯甲醛和苄胺的-C-H氟烷氧基化反应。在亲电氟化旁观氧化剂和氟化醇的存在下，多种苯甲醛和苄胺能够在邻位选择性地进行氧化反应，从而得到氟代烷基芳基醚。这种巧妙的方法将为药物分子和天然产物的合成提供有吸引力的策略。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8333/9235058/6d575467cdf0/d2ra00241h-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8333/9235058/6248c1f652fb/d2ra00241h-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8333/9235058/e8b7e34986cf/d2ra00241h-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8333/9235058/8d42645e8509/d2ra00241h-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8333/9235058/6d575467cdf0/d2ra00241h-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8333/9235058/6248c1f652fb/d2ra00241h-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8333/9235058/e8b7e34986cf/d2ra00241h-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8333/9235058/8d42645e8509/d2ra00241h-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8333/9235058/6d575467cdf0/d2ra00241h-s4.jpg

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