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Organic letters. 2025 May 29. doi: 10.1021/acs.orglett.5c01555 Q15.02025

Ni-H-Catalyzed Regioselective Hydroalkylation of Terminal Alkynes with α-Bromo Phosphonates

镍氢催化的末端炔烃与α-溴磷onic酯的区域选择性加成氢烷基化反应 翻译改进

Huimin Yang  1, Niannian Li  1, Jiayan Jin  1, Yang Ye  1

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作者单位

  • 1 School of Pharmacy, Hangzhou Normal University, Hangzhou, Zhejiang 311121, PR China.
  • DOI: 10.1021/acs.orglett.5c01555 PMID: 40438913

    摘要 中英对照阅读

    We present here a versatile and efficient Ni-H-catalyzed hydroalkylation reaction of terminal alkynes and α-bromo phosphonates with Markovnikov selectivity, yielding a range of allylic phosphate terminal alkenes. This reaction demonstrates a broad substrate scope and excellent functional group compatibility, including those with complex structural motifs found in natural products and pharmaceuticals. The practical applicability is demonstrated through gram-scale reactions and product transformations. In addition, the methodology is also applicable to the substrates of benzyl bromides and bromo amides.

    Keywords:ni-h catalysis; hydroalkylation; terminal alkynes; bromo phosphonates; regioselectivity

    在这里,我们介绍了一种通用且高效的Ni-H催化体系,用于末端炔烃和α-溴磷onic酸酯的Markovnikov选择性氢烷基化反应,生成一系列烯丙基磷酸酯终端烯烃。该反应展示了广泛的底物范围和出色的官能团兼容性,包括天然产物和药物中发现的复杂结构基序。通过克级反应和产品转化证明了其实用性。此外,该方法还适用于苯甲基溴化物和溴胺衍生物的底物。

    关键词:镍催化的氢官能团化; 氢烷基化; 末端炔烃; 溴代磷腈; 区域选择性

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    期刊名:Organic letters

    缩写:ORG LETT

    ISSN:1523-7060

    e-ISSN:1523-7052

    IF/分区:5.0/Q1

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    Ni-H-Catalyzed Regioselective Hydroalkylation of Terminal Alkynes with α-Bromo Phosphonates