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.
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
作者单位 +展开
作者单位
DOI: 10.1021/acs.orglett.5c01555 PMID: 40438913
摘要 中英对照阅读
相关内容
-
Copper-catalyzed hydroalkylation of terminal alkynes
末端炔烃的铜催化氢官能化反应
Journal of the American Chemical Society. 2015 Feb 4;137(4):1424-7.
-
Mechanism of Z-Selective Hydroalkylation of Terminal Alkynes
末端炔烃Z-选择性氢烷基化的机制
Journal of the American Chemical Society. 2021 Oct 13;143(40):16663-16672.
-
Copper-catalyzed aminothiolation of terminal alkynes with tunable regioselectivity
可调控区域选择性的末端炔烃与氨基硫醇的铜催化偶联反应
Chemical communications (Cambridge, England). 2019 Feb 5;55(12):1813-1816.
-
Copper-Catalyzed anti-Markovnikov Hydroindolation of Terminal Alkynes: Regioselective Synthesis of Bis(indolyl)alkanes
铜催化末端炔烃的反马尔科夫尼可夫氢吲哚化反应:双(吲哚基)烷烃的选择性合成
The Journal of organic chemistry. 2016 Dec 2;81(23):11664-11670.
-
Rhodium-Catalyzed Hydrophosphorylation of Terminal Alkynes Leading to Highly Selective Formation of (E)-Alkenylphosphonates: Complete Reversal of Regioselectivity to the Palladium-Catalyzed Counterpart We are grateful to the Japan Science and Technology Corporation (JST) for financial support through the CREST (Core Research for Evolutional Science and
铑催化末端炔烃的水相磷基化反应高选择性地生成(E)烯基膦酸酯:与钯催化体系区域选择性的完全转换日本科学技术振兴集团(CREST)资助项目的一部分研究成果
Angewandte Chemie (International ed. in English). 2001 May 18;40(10):1929-1932.
-
NiH-Catalyzed Regio- and Enantioselective Hydroalkylation for the Synthesis of β- or γ-Branched Chiral Aromatic N-Heterocycles
镍催化的区域选择性和enantioselective hydroalkylation合成β-或γ-分支的手性芳香N杂环
Journal of the American Chemical Society. 2023 Oct 11;145(40):22122-22134.
-
Indium catalyzed tandem hydroamination/hydroalkylation of terminal alkynes
末端炔烃的吲哚催化串联羟胺化/羟基烷基化反应
Chemical communications (Cambridge, England). 2011 Sep 7;47(33):9525-7.
-
Copper-Catalyzed Regio- and Stereoselective 1,1-Dicarbofunctionalization of Terminal Alkynes
铜催化末端炔烃区域选择性和立体选择性双官能化反应生成联芳基乙酸酯类化合物研究进展
Organic letters. 2019 Aug 2;21(15):6034-6039.
-
Regio- and stereoselective hydrosilylation of terminal alkynes using Grubbs' first-generation olefin-metathesis catalyst
利用Grubbs第一代烯烃复分解催化剂对末端炔烃进行区域和立体选择性氢硅化反应
Organic & biomolecular chemistry. 2004 Sep 21;2(18):2558-62.