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Synthesis of β-ketonitriles, α,β-alkynones and biscabinols from esters using tert-butoxide-assisted C(=O)-C (i.e., acyl-C) coupling under ambient conditions
被引:19
|作者:
Kim, Bo Ram
[1
]
Lee, Hyung-Geun
[1
]
Kang, Seung-Beom
[1
]
Jung, Kwang-Ju
[1
]
Sung, Gi Hyeon
[1
]
Kim, Jeum-Jong
[2
]
Lee, Sang-Gyeong
[1
]
Yoon, Yong-Jin
[1
]
机构:
[1] Gyeongsang Natl Univ, Res Inst Nat Sci, Dept Chem, Jinju 660701, South Korea
[2] Elect & Telecommun Res Inst, Adv Solar Technol Res Dept, Taejon 305700, South Korea
来源:
关键词:
alpha;
beta-Alkynylketone;
Aryl bis(phenylethynyl)carbinols;
tert-Butoxide-assisted reaction;
C(=O)-C coupling;
beta-Ketonitriles;
PALLADIUM-CATALYZED REARRANGEMENT;
AEROBIC OXIDATION;
BOND FORMATION;
KETONES;
ACID;
CHEMISTRY;
CHLORIDES;
EFFICIENT;
REAGENTS;
D O I:
10.1016/j.tet.2013.10.007
中图分类号:
O62 [有机化学];
学科分类号:
070303 ;
081704 ;
摘要:
We demonstrated the synthesis of beta-ketonitriles, alpha,beta-alkynones, and biscarbinols using tert-butoxideassisted C(C=O)-C (i.e., acyl-C) coupling of esters under ambient conditions. tert-Butoxide-assisted C(C=O)-C (i.e., acyl-C) coupling of esters with cyanomethylenes and acetylenes under transition metalfree ambient conditions gives beta-ketonitriles, alpha,beta-alkynones and/or aryl bis(phenylethynyl)carbinols in moderate-to-good yields. It is noteworthy that this is a rapid, facile, and efficient process under ambient conditions, and use of cheap and stable starting materials. (C) 2013 Elsevier Ltd. All rights reserved.
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页码:10331 / 10336
页数:6
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