Synthesis of (Z)-β-halo α,β-unsaturated carbonyl systems via the combination of halotrimethylsilane and tetrafluoroboric acid
作者： Vitor A. F. da Silva , Gustavo P. da Silva , Bianca T. Matsuo , Akbar Ali , Rebecca L. Davis
DOI: 10.1039/C8OB02110D
关键词:
摘要: A convenient and broadly applicable method for the hydrohalogenation of ynones is described, by combination halotrimethylsilanes tetrafluoroboric acid. Practically, one equivalent HX (Bronsted acid) BF3 (Lewis smoothly generated, which activates carbonyl compounds. Through this protocol, 42 examples (Z)-β-halovinyl compounds (Cl, Br I) were obtained, in good yields high stereoselectivity having 2-MeTHF as a solvent.
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Hun Young Kim, Kyungsoo Oh, A facile access to 4-substituted-2-naphthols via a tandem Friedel-Crafts reaction: a β-chlorovinyl ketone pathway. Organic Letters. ,vol. 16, pp. 5934- 5936 ,(2014) , 10.1021/OL502951V
R. A. Gadzhili, A. G. Aliev, R. A. Nadzhafova, R. I. Ibragimov, Interaction of 3-Chloro-2-halopropenyl Ketones with β-Aminocrotonic Acid Ethyl Ester Chemistry of Heterocyclic Compounds. ,vol. 41, pp. 1009- 1012 ,(2005) , 10.1007/S10593-005-0269-2
Michael P. Doyle, Alvaro H. Devia, Kathlene E. Bassett, Jan W. Terpstra, Surendra N. Mahapatro, Unsymmetrical alkenes by carbene coupling from diazirine decomposition in the presence of diazo compounds Journal of Organic Chemistry. ,vol. 52, pp. 1619- 1621 ,(1987) , 10.1021/JO00384A049
Tomohiro Iwai, Tetsuaki Fujihara, Jun Terao, Yasushi Tsuji, Iridium-Catalyzed Addition of Acid Chlorides to Terminal Alkynes Journal of the American Chemical Society. ,vol. 131, pp. 6668- 6669 ,(2009) , 10.1021/JA901778Y
V. A. Kobelevskaya, L. I. Larina, A. V. Popov, E. V. Rudyakova, G. G. Levkovskaya, Synthesis and structure of 1-tert-butyl-substituted 3(5)-alkylpyrazoles from 2-chlorovinyl ketones Russian Journal of Organic Chemistry. ,vol. 51, pp. 231- 239 ,(2015) , 10.1134/S1070428015020177
Nitya G. Kundu, Lakshmi N. Chaudhuri, Synthesis of dimethoxypyrimidines and uracils with novel C-5 substituents Journal of the Chemical Society, Perkin Transactions 1. pp. 1677- 1682 ,(1991) , 10.1039/P19910001677
Bo Wang, Shihua Wang, Pinhua Li, Lei Wang, Iron-catalyzed regio- and stereoselective addition of acid chlorides to alkynes Chemical Communications. ,vol. 46, pp. 5891- 5893 ,(2010) , 10.1039/C0CC01182G
Hun Young Kim, Seokwoo Lee, Sanghee Kim, Kyungsoo Oh, Regiodivergent halogenation of (E)-β-chlorovinyl ketones via soft α-vinyl enolization strategy. Organic Letters. ,vol. 17, pp. 450- 453 ,(2015) , 10.1021/OL5034354
Andrey O. Shchukin, Aleksander V. Vasilyev, Different reactivities of acetylene carbonyl compounds under the catalysis by Bronsted superacids and Lewis acids Applied Catalysis A-general. ,vol. 336, pp. 140- 147 ,(2008) , 10.1016/J.APCATA.2007.07.035
Parthasarathy Gandeepan, Kanniyappan Parthasarathy, Tsu-Hui Su, Chien-Hong Cheng, Iron‐Catalyzed Synthesis of β‐Chlorovinyl and α,β‐Alkynyl Ketones from Terminal and Silylated Alkynes with Acid Chlorides Advanced Synthesis & Catalysis. ,vol. 354, pp. 457- 468 ,(2012) , 10.1002/ADSC.201100670