光诱导芳基酮通过协同同溶芳香族取代催化醚和 N-叔丁氧羰基胺杂原子上的 C(sp3)-H 键的苯化作用

Synthesis Pub Date : 2024-06-04 DOI:10.1055/a-2338-4243
Masaya Azami, Michinori Sumimoto, Reika Nakamura, T. Murafuji, Shin Kamijo
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引用次数: 0

摘要

利用光激发 4-苯甲酰基吡啶作为氢原子转移 (HAT) 催化剂,在醚和 N-叔丁氧羰基胺杂原子上的非酸性 C(sp3)-H键处实现了一步苯化反应。设计缺电子的(三氟甲基磺酰基)苯衍生物作为苯基前体对于实现当前的转化至关重要。此外,DFT 计算表明,目前的转化是通过协同均解芳香取代进行的,而不是通过逐步形成环己二烯自由基中间体进行的。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Photoinduced Aryl Ketone-Catalyzed Phenylation of C(sp3)–H Bonds Attached to the Heteroatom of Ethers and N-Boc-amines via Concerted Homolytic Aromatic Substitution

Photoinduced Aryl Ketone-Catalyzed Phenylation of C(sp3)–H Bonds Attached to the Heteroatom of Ethers and N-Boc-amines via Concerted Homolytic Aromatic Substitution
A single-step phenylation at the non-acidic C(sp3)–H bond attached to the heteroatom of ethers and N-Boc-amines has been achieved using photoexcited 4-benzoylpyridine as a hydrogen atom transfer (HAT) catalyst. The design of electron-deficient (trifluoromethylsulfonyl)benzene derivatives, as a phenyl precursor, was critical to realizing the present transformation. Moreover, the DFT calculation indicated that the present transformation proceeds via a concerted homolytic aromatic substitution rather than via a stepwise one involving the formation of a cyclohexadienyl radical intermediate.
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