Zinc-Catalyzed Dehydrogenative Cross-Coupling of Terminal Alkynes with Aldehydes: Access to Ynones

被引:45
作者
Tang, Shan [1 ]
Zeng, Li [1 ]
Liu, Yichang [1 ]
Lei, Aiwen [1 ,2 ]
机构
[1] Wuhan Univ, Inst Adv Studies, Coll Chem & Mol Sci, Wuhan 430072, Hubei, Peoples R China
[2] Jiangxi Normal Univ, Natl Res Ctr Carbohydrate Synth, Nanchang 330022, Peoples R China
基金
高等学校博士学科点专项科研基金; 中国国家自然科学基金;
关键词
C-H activation; cross-coupling; dehydrogenation; homogeneous catalysis; zinc; ALPHA-KETO ACIDS; DECARBOXYLATIVE ALKYNYLATION; PROPARGYLIC ALCOHOLS; SONOGASHIRA REACTION; DIRECT ADDITION; ACTIVATION; CONVENIENT; GENERATION; DISCOVERY; REAGENTS;
D O I
10.1002/anie.201509042
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Because of the lack of redox ability, zinc has seldom been used as a catalyst in dehydrogenative cross-coupling reactions. Herein, a novel zinc-catalyzed dehydrogenative C(sp(2))-H/C(sp)-H cross-coupling of terminal alkynes with aldehydes was developed, and provides a simple way to access ynones from readily available materials under mild reaction conditions. Good reaction selectivity can be achieved with a 1: 1 ratio of terminal alkyne and aldehyde. Various terminal alkynes and aldehydes are suitable in this transformation.
引用
收藏
页码:15850 / 15853
页数:4
相关论文
共 50 条
  • [21] Palladium-Catalyzed Oxidative Cross-Coupling between Heterocycles and Terminal Alkynes with Low Catalyst Loading
    Jie, Xiaoming
    Shang, Yaping
    Hu, Peng
    Su, Weiping
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (13) : 3630 - 3633
  • [22] Palladium-catalyzed cross-coupling of arylcarboxylic acid 2-pyridyl esters with terminal alkynes
    Yu, Hang
    Nie, Jing-Jing
    Wang, Zhong-Xia
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (44) : 8764 - 8772
  • [23] Palladium-Catalyzed Cross-Coupling Reaction of Bis(cyclopentadienyl)diaryltitaniums with Terminal Alkynes
    Murata, Yuki
    Nishi, Yuya
    Matsumura, Mio
    Yasuike, Shuji
    REACTIONS, 2023, 4 (04): : 657 - 666
  • [24] Cross-coupling of arylboronic acids with terminal alkynes in air
    Zou, G
    Zhu, JR
    Tang, J
    TETRAHEDRON LETTERS, 2003, 44 (48) : 8709 - 8711
  • [25] Facile synthesis of substituted alkynes by cyclopalladated ferrocenylimine catalyzed cross-coupling of arylboronic acids/esters with terminal alkynes
    Yang, Fan
    Wu, Yangjie
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (21) : 3476 - 3479
  • [26] Palladium-catalyzed dehydrogenative coupling of terminal alkynes with secondary phosphine oxides
    Yang, Jia
    Chen, Tieqiao
    Zhou, Yongbo
    Yin, Shuangfeng
    Han, Li-Biao
    CHEMICAL COMMUNICATIONS, 2015, 51 (17) : 3549 - 3551
  • [27] A Drastic Effect of TEMPO in Zinc-Catalyzed Stannylation of Terminal Alkynes with Hydrostannanes via Dehydrogenation and Oxidative Dehydrogenation
    Kai, Yuichi
    Oku, Shinya
    Tani, Tomohiro
    Sakurai, Kyoko
    Tsuchimoto, Teruhisa
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (18) : 4314 - 4323
  • [28] Synthesis of Pyrrole-Annulated Heterocycles through Copper-Catalyzed Site-Selective Dehydrogenative Cross-Coupling
    Tripathi, Krishna N.
    Ray, Devalina
    Singh, Ravi P.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (38) : 5809 - 5813
  • [29] Copper-catalyzed homo- and cross-coupling reactions of terminal alkynes in ethyl lactate
    Wan, Jie-Ping
    Cao, Shuo
    Jing, Yanfeng
    APPLIED ORGANOMETALLIC CHEMISTRY, 2014, 28 (08) : 631 - 634
  • [30] Cu(I)-catalyzed aerobic cross-dehydrogenative coupling of terminal alkynes with thiols for the construction of alkynyl sulfides
    Yang, Yong
    Dong, Weibing
    Guo, Yisong
    Rioux, Robert M.
    GREEN CHEMISTRY, 2013, 15 (11) : 3170 - 3175