Zirconium-Catalyzed Synthesis of 6-(Trifluoromethyl)-2H-pyran-2-ones via C-C Bond Cleavage

被引：1

作者：

Zhang, Zipeng ^{[1
,2
,3
]}

Huang, Yangjie ^{[1
,2
]}

Yuan, Zihang ^{[3
]}

Xia, Jianrong ^{[1
,2
]}

Weng, Zhiqiang ^{[1
,2
,3
]}

机构：

[1] Minjiang Univ, Fujian Prov Univ, Coll Mat & Chem Engn, Engn Res Ctr Green Mat & Chem Eng, Fuzhou 350108, Peoples R China

[2] Minjiang Univ, Fujian Engn Res Ctr New Chinese Lacquer Mat, Fuzhou 350108, Peoples R China

[3] Fuzhou Univ, Coll Chem, Key Lab Mol Synth & Funct Discovery, Fuzhou 350108, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 08期

基金：

中国国家自然科学基金;

关键词：

ONE-POT SYNTHESIS; ALPHA-PYRONES; INSERTION;

D O I：

10.1021/acs.joc.4c00227

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A strategy for the annulation reaction of alkynones with ethyl 4,4,4-trifluoro-3-oxobutanoate through C-C bond cleavage is described. The zirconium-catalyzed transformation provides access to a wide range of structurally diverse 6-(trifluoromethyl)-2H-pyran-2-ones in moderate to good yields, utilizing Na2CO3 as a base. Further transformations into trifluoromethylated arene derivatives have been demonstrated as well. Furthermore, plausible reaction pathways are proposed by conducting various control experiments and isolating a beta-diketone intermediate (X-ray) containing an intramolecular hydrogen bond.

引用

页码：5683 / 5689

页数：7

共 50 条

[21] Palladium-Catalyzed Skeletal Rearrangement of Cyclobutanones via C-H and C-C Bond Cleavage
Ano, Yusuke
Takahashi, Daichi
Yamada, Yuki
Chatani, Naoto
ACS CATALYSIS, 2023, 13 (04) : 2234 - 2239
[22] Versatile Synthesis of Functionalized Tetrahydroisoquinolines by Ring Transformation of 2H-Pyran-2-ones
Kole, Priyanka B.
Singh, Fateh V.
AUSTRALIAN JOURNAL OF CHEMISTRY, 2019, 72 (07) : 524 - 532
[23] Ru(II)-Catalyzed Tunable Cascade Reaction via C-H/C-C Bond Cleavage
Yang, Zi
Yue, Qi
Yang, Mengqi
Zhang, Hong
Cui, Xiuling
JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (20): : 12960 - 12970
[24] A SIMPLE AND GENERAL ONE-POT SYNTHESIS OF SOME 2H-PYRAN-2-ONES AND FUSED PYRAN-2-ONES
KEPE, V
KOCEVAR, M
POLANC, S
VERCEK, B
TISLER, M
TETRAHEDRON, 1990, 46 (06) : 2081 - 2088
[25] Easy and green synthesis of 6-(arylvinyl)-4-hydroxy-3-(phenylsulfanyl)-2H-pyran-2-ones in aqueous potassium hydroxide
N. Benferrah
M. Hammadi
F. Berthiol
Russian Journal of General Chemistry, 2016, 86 : 2881 - 2886
[26] ACYL ANION EQUIVALENTS IN THE SYNTHESIS OF 2H-PYRAN-2-ONES - AN EFFICIENT SYNTHESIS OF ANIBINE
DHAVALE, DD
AIDHEN, IS
SHAFIQUE, M
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (16): : 3985 - 3987
[27] Copper oxide catalyzed domino process for the synthesis of substituted 2H-pyran-2-ones and polyhydroxy coumarin derivatives
Kayal, Utpal
Karmakar, Rajiv
Banerjee, Dipanwita
Maiti, Gourhari
TETRAHEDRON, 2014, 70 (39) : 7016 - 7021
[28] Rhodium-catalyzed alkenylation of allylbenzenes via C-C bond cleavage
Kakiuchi, Fumitoshi
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 257
[29] Synthesis of benzocyclobutanes through ring transformation reactions of 2H-pyran-2-ones
Sil, D
Sharon, A
Pratap, R
Maulik, PR
Ram, VJ
SYNLETT, 2004, (12) : 2163 - 2164
[30] ALPHA-PYRONES .3. SYNTHESIS OF 5,6-DIHYDRO-1 H-BENZO[C]-QUINOLIZIN-1-ONES FROM 6-(2-NITROSTYRYL)-2H-PYRAN-2-ONES
GELMI, ML
POCAR, D
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1993, 30 (02) : 483 - 485

← 1 2 3 4 5 →