Metal-Free Decarboxylation of Alkynoic Acids for the Synthesis of Terminal Alkynes

被引:5
作者
Seo, Eunkyeong [1 ]
Oh, Jonghoon [1 ]
Lee, Sunwoo [1 ]
机构
[1] Chonnam Natl Univ, Dept Chem, Gwangju 61186, South Korea
基金
新加坡国家研究基金会;
关键词
decarboxylation; terminal alkyne; alkynoic aicd; deuteration; metal-free conditions; ONE-POT CONVERSION; CARBOXYLIC-ACIDS; ALKYNYLATION; HALIDES;
D O I
10.1002/ajoc.202000363
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Terminal alkynes were readily obtained via the reaction of alkynoic acids withN,N,N',N'-teramethylethylenediamine (TMEDA) in DMSO at 65 degrees C for 12 h. This method gave good yields and showed high functional group tolerance. In addition, deuterated terminal alkynes were formed in good yields when alkynoic acids were treated with D2O prior to the reaction with TMEDA.
引用
收藏
页码:1774 / 1777
页数:4
相关论文
共 37 条
[21]   Transition metal-catalyzed decarboxylative coupling reactions of alkynyl carboxylic acids [J].
Park, Kyungho ;
Lee, Sunwoo .
RSC ADVANCES, 2013, 3 (34) :14165-14182
[22]   Palladium-Catalyzed Sonogashira Reaction for the Synthesis of Arylalkynecarboxylic Acids from Aryl Bromides at Low Temperature [J].
Park, Kyungho ;
You, Jung-Min ;
Jeon, Seungwon ;
Lee, Sunwoo .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (10) :1973-1978
[23]   Synthesis of aryl alkynyl carboxylic acids and aryl allrynes from propiolic acid and aryl halides by site selective coupling and decarboxylation [J].
Park, Kyungho ;
Palani, Thiruvengadam ;
Pyo, Ayoung ;
Lee, Sunwoo .
TETRAHEDRON LETTERS, 2012, 53 (07) :733-737
[24]   Organocatalytic asymmetric direct α-alkynylation of cyclic β-ketoesters [J].
Poulsen, Thomas B. ;
Bernardi, Luca ;
Aleman, Jose ;
Overgaard, Jacob ;
Jorgensen, Karl Anker .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (02) :441-449
[25]   One-pot conversion of activated alcohols into terminal alkynes using manganese dioxide in combination with the Bestmann-Ohira reagent [J].
Quesada, E ;
Taylor, RJK .
TETRAHEDRON LETTERS, 2005, 46 (38) :6473-6476
[26]   Further improvements of the synthesis of alkynes from aldehydes [J].
Roth, GJ ;
Liepold, B ;
Müller, SG ;
Bestmann, HJ .
SYNTHESIS-STUTTGART, 2004, (01) :59-62
[27]   Triazabicyclodecene:: An effective isotope exchange catalyst in CDCl3 [J].
Sabot, Cyrille ;
Kumar, Kanduluru Ananda ;
Antheaume, Cyril ;
Mioskowski, Charles .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (13) :5001-5004
[28]   Synthesis of arenediynes via the vinylidenecarbene-acetylene rearrangement [J].
Sahu, B ;
Namboothiri, INN ;
Persky, R .
TETRAHEDRON LETTERS, 2005, 46 (15) :2593-2597
[29]   Synthetic and mechanistic investigations on the rearrangement of 2,3-unsaturated 1,4-bis(alkylidene)carbenes to enediynes [J].
Sahu, Bichismita ;
Muruganantham, Rajendran ;
Namboothiri, Irishi N. N. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (15) :2477-2489
[30]   IMPROVED LABORATORY METHOD FOR PREPARATION OF DIACETYLENE [J].
TEDESCHI, RJ ;
BROWN, AE .
JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (07) :2051-&