Photoelectrochemical Iron-Catalyzed C(sp3)–H Borylation of Alkanes in a Position-Selective Manner

IF 9.4 1区 化学 Q1 CHEMISTRY, MULTIDISCIPLINARY CCS Chemistry Pub Date : 2024-03-28 DOI:10.31635/ccschem.024.202403894
Wen Wei, Bin Wang, Simon L. Homölle, Jinbin Zhu, Yanjun Li, Tristan von Münchow, Isaac Maksso, Lutz Ackermann
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Abstract

Catalytic C–H borylation is of prime topical importance, since easily available feedstock chemicals can thereby be transformed into valuable transient functional groups in the absence of directing groups. Herein, we disclose an iron-catalyzed C(sp3)–H borylation of simple, non-prefunctionalized alkanes, providing access to value-added products in a single step by means of photoelectrochemistry. The power of merging photo- and electrochemistry was mirrored by ample scope and exceedingly mild reaction conditions. Moreover, an outstanding position-selectivity in favor of primary C(sp3)–H proved viable within the photoelectrochemical borylation through a chemo-selective anodic overoxidation manifold. The ferro-photoelectrochemistry strategy avoids toxic precious transition metals, enabling C(sp3)–H borylations in a site-selective fashion.

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光电化学铁催化 C(sp3)-H 位置选择性烷烃的 Borylation
催化 C-H borylation 具有重要的现实意义,因为在没有定向基团的情况下,容易获得的原料化学品可以因此转化为有价值的瞬时官能团。在此,我们公开了一种铁催化的简单、非官能化烷烃的 C(sp3)-H borylation,通过光电化学,一步即可获得高附加值产品。光化学和电化学相结合的优势体现在反应范围广、反应条件极其温和。此外,事实证明,通过化学选择性阳极过氧化歧管,光电化学硼烷基化反应对主 C(sp3)-H 具有出色的位置选择性。这种铁基光电化学策略避免了有毒的贵重过渡金属,从而以位点选择性的方式实现了 C(sp3)-H 硼酰化。
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来源期刊
CCS Chemistry
CCS Chemistry Chemistry-General Chemistry
CiteScore
13.60
自引率
13.40%
发文量
475
审稿时长
10 weeks
期刊介绍: CCS Chemistry, the flagship publication of the Chinese Chemical Society, stands as a leading international chemistry journal based in China. With a commitment to global outreach in both contributions and readership, the journal operates on a fully Open Access model, eliminating subscription fees for contributing authors. Issued monthly, all articles are published online promptly upon reaching final publishable form. Additionally, authors have the option to expedite the posting process through Immediate Online Accepted Article posting, making a PDF of their accepted article available online upon journal acceptance.
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