A General Access to Propargylic Ethers through BrOnsted Acid Catalyzed Alkynylation of Acetals and Ketals with Trifluoroborates

Baxter Matthew; Bolshan Yuri

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A General Access to Propargylic Ethers through BrOnsted Acid Catalyzed Alkynylation of Acetals and Ketals with Trifluoroborates

机译：通过布朗斯台德酸催化的乙醛和缩酮与三氟硼酸酯的炔基化反应，可获得炔丙基醚

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A general BrOnsted acid catalyzed methodology for the alkynylation of acetals and ketals with alkynyltrifluoroborate salts has been developed. The reaction proceeds rapidly to afford valuable synthetic building block propargylic ethers in good to excellent yields. Unlike Lewis acid catalyzed transformations of trifluoroborates, this approach does not proceed via unstable organodifluoroborane intermediate. As a result, the developed methodology features excellent functional group tolerance and good atom economy.

机译：已经开发出用于用乙炔基三氟硼酸盐将乙缩醛和缩酮烷基化的一般布朗斯台德酸催化方法。反应进行得很快，从而以高至优异的产率提供了有价值的合成砌块炔丙基醚。与路易斯酸催化的三氟硼酸酯的转化不同，该方法不会通过不稳定的有机二氟硼烷中间体进行。结果，所开发的方法具有出色的官能团耐受性和良好的原子经济性。

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《Chemistry: A European journal》 |2015年第39期|共4页
作者
Baxter Matthew; Bolshan Yuri;
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正文语种 eng
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关键词
alkynylation; borates; BrOnsted acids; propargylic ethers;

机译：炔基化;硼酸盐;布朗斯台德酸;炔丙基醚;

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1. A General Access to Propargylic Ethers through BrOnsted Acid Catalyzed Alkynylation of Acetals and Ketals with Trifluoroborates [J] . Baxter Matthew, Bolshan Yuri Chemistry: A European journal . 2015,第39期

机译：通过布朗斯台德酸催化的乙醛和缩酮与三氟硼酸酯的炔基化反应，可获得炔丙基醚
2. Palladium Chloride-Catalyzed Reductive Cleavage of Benzylic Acetal, Ketal and Ether Compounds with Triethylsilane [J] . M. Mirza-Aghayan, R. Boukherroub, M. Rahimifard, Journal of the Iranian Chemical Society . 2011,第2期

机译：氯化钯催化的三乙基硅烷对乙缩醛，缩酮和醚化合物的还原裂解
3. Palladium and Bronsted Acid Co-Catalyzed Biginelli-like Multicomponent Reactions via in Situ-Generated Cyclic Enol Ether: Access to Spirofuran-hydropyrimidinones [J] . Yu Shuyan, Wu Jingxin, Lan Hongbing, Organic letters . 2020,第1期

机译：通过原位产生的环烯醚（肺酸酸）和铜硬脂酸通过原位产生的循环烯乙醚助催化的大蛋白酸多的多组分反应：获得螺呋喃 - 氢吡啶啉酮
4. Synthesis of acetals and ketals catalyzed by H4SiW6Mo6O40/SiO2 [C] . Shuijin Yang, Li YU, Yongkui Huang, International conference on Frontiers of advanced materials and engineering technology . 2012

机译：H4SiW6Mo6O40 / SiO2催化合成乙缩醛和缩酮
5. Rhodium and Platinum Catalyzed Cycloadditions from Propargylic Esters and Ethers [D] . Shu, Dongxu 2013

机译：炔丙基酯和醚的铑和铂催化的环加成反应
6. Palladium-Catalyzed Enantioselective Redox-Relay Heck Alkynylation of Alkenols to Access Propargylic Stereocenters [O] . Dr. Zhi-Min Chen, Christine S. Nervig, Dr. Ryan J. DeLuca, -1

机译：钯催化的烯醇的对映体选择性氧化还原-中继Heck炔基化反应以达到炔丙基立体中心。
7. Relative reactivities of acetals and orthoesters in Lewis acid catalyzed reactions with vinyl ethers. A systematic investigation of the synthetic potential of acetals and orthoesters in electrophilic alkoxyalkylations of enol ethers [O] . Brüggen Uwe von der, Lammers Roswitha, Mayr Herbert 1988

机译：路易斯酸催化乙烯基醚反应中缩醛和原酸酯的相对反应性。系统研究缩醛和原酸酯在烯醇醚的亲电烷氧基烷基化中的合成潜力

A General Access to Propargylic Ethers through BrOnsted Acid Catalyzed Alkynylation of Acetals and Ketals with Trifluoroborates

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