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
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.
引用
收藏
页码:10331 / 10336
页数:6
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