软-硬酸碱控制的、氧化的、通过硝鎓离子的 N-选择性芳基化反应磺酰胺。
Soft-Hard Acid/Base-Controlled, Oxidative, N-Selective Arylation of Sulfonanilides via a Nitrenium Ion.
机构信息
School of Chemical Sciences, National Institute of Science Education and Research (NISER), HBNI, Bhubaneswar , PO Bhimpur-Padanpur, Via Jatni, District Khurda, Odisha 752050, India.
出版信息
J Org Chem. 2018 Feb 2;83(3):1340-1347. doi: 10.1021/acs.joc.7b02841. Epub 2018 Jan 19.
In iodine(III)-catalyzed, dehydrogenative arylations of sulfonanilides, the functionalization of C-C bonds is preferred over the functionalization of C-N bonds. Herein, an unprecedented N-selective arylation of sulfonanilides using soft-hard acid-base (SHAB) control by a nitrenium ion over a carbenium ion is reported. Treatment of sulfonanilides with iodine(III) led to the formation of nitrenium ions (soft), which preferentially react with biphenyls (soft) over bimesityl (hard) to generate C-N bonds. The iodine(III) was generated in situ by using PhI and mCPBA at room temperature.
在碘(III)催化的磺酰苯胺脱氢芳基化反应中，C-C 键的功能化优先于 C-N 键的功能化。在此，报道了一种前所未有的通过氮宾离子对碳正离子的软硬酸碱（SHAB）控制，实现磺酰苯胺的 N-选择性芳基化反应。用碘(III)处理磺酰苯胺，生成氮宾离子（软），它优先与联苯（软）反应，而不是与均三甲苯（硬）反应，生成 C-N 键。碘(III)是通过室温下使用 PhI 和 mCPBA 原位生成的。
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