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Multicomponent synthesis of tertiary alkylamines by photocatalytic olefin-hydroaminoalkylation

机译：光催化烯烃-氢氨基烷基化多组分合成叔烷基胺

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摘要

There is evidence to suggest that increasing the level of saturation (that is, the number of sp(3)-hybridized carbon atoms) of small molecules can increase their likelihood of success in the drug discovery pipeline(1). Owing to their favourable physical properties, alkylamines have become ubiquitous among pharmaceutical agents, small-molecule biological probes and pre-clinical candidates(2). Despite their importance, the synthesis of amines is still dominated by two methods: N-alkylation and carbonyl reductive amination(3). Therefore, the increasing demand for saturated polar molecules in drug discovery has continued to drive the development of practical catalytic methods for the synthesis of complex alkylamines(4-7). In particular, processes that transform accessible feedstocks into sp(3)-rich architectures provide a strategic advantage in the synthesis of complex alkylamines. Here we report a multicomponent, reductive photocatalytic technology that combines readily available dialkylamines, carbonyls and alkenes to build architecturally complex and functionally diverse tertiary alkylamines in a single step. This olefin-hydroaminoalkylation process involves a visible-light-mediated reduction of in-situ-generated iminium ions to selectively furnish previously inaccessible alkyl-substituted a-amino radicals, which subsequently react with alkenes to form C(sp(3))-C(sp(3)) bonds. The operationally straightforward reaction exhibits broad functional-group tolerance, facilitates the synthesis of drug-like amines that are not readily accessible by other methods and is amenable to late-stage functionalization applications, making it of interest in areas such as pharmaceutical and agrochemical research.
机译：有证据表明，增加小分子的饱和度（即，sp（3）-杂化碳原子的数量）可以增加其在药物开发管线中成功的可能性（1）。由于其良好的物理性能，烷基胺已在药剂，小分子生物探针和临床前候选物中普遍存在（2）。尽管它们的重要性，但胺的合成仍以两种方法主导：N-烷基化和羰基还原胺化（3）。因此，药物开发中对饱和极性分子的需求不断增长，继续推动了用于合成复杂烷基胺的实用催化方法的发展（4-7）。特别是，将可获取的原料转化为富含sp（3）的体系结构的过程在合成复杂的烷基胺中提供了战略优势。在这里，我们报告了一种多组分还原性光催化技术，该技术结合了容易获得的二烷基胺，羰基化合物和烯烃，可在单个步骤中构建出结构复杂且功能多样的叔烷基胺。该烯烃-氢氨基烷基化过程涉及可见光介导的原位生成的亚胺离子的还原，以选择性地提供先前难以获得的烷基取代的α-氨基自由基，该自由基随后与烯烃反应形成C（sp（3））-C （sp（3））债券。操作简单的反应显示出宽泛的官能团耐受性，促进了其他方法不易获得的药物样胺的合成，并且适合后期功能化应用，这使其在诸如制药和农业化学研究等领域受到关注。

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  • 来源
    《Nature》 |2018年第7724期|522-527|共6页
  • 作者

    Trowbridge Aaron; Reich Dominik; Gaunt Matthew J.;

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  • 收录信息 美国《科学引文索引》(SCI);美国《工程索引》(EI);美国《生物学医学文摘》(MEDLINE);美国《化学文摘》(CA);
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