An Efficient Synthesis of Terminal Allenes from Terminal 1-Alkynes

被引:153
作者
Kuang, Jinqiang
Ma, Shengming [1 ]
机构
[1] E China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Dept Chem, Shanghai 200062, Peoples R China
基金
中国国家自然科学基金;
关键词
CATALYZED REACTIONS; PROPARGYLIC AMINES; CYCLIZATION; ARYL; 3,4-ALLENOLS; ALCOHOLS; HALIDES; KETONES; ALKYNES;
D O I
10.1021/jo802391x
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We have developed a modified method for the synthesis of terminal allenes from terminal 1-alkyne: The reaction of 1-alkynes with 1.8 equiv of Cy2NH and 2.5 equiv of paraformaldehyde mediated by CuI (0.5 equiv) in refluxing dioxane may produce terminal allenes in much higher yields than the previously reported protocol and many functional groups such as mesylate, hydroxyl group, ether, amide, etc. may be tolerated.
引用
收藏
页码:1763 / 1765
页数:3
相关论文
共 41 条
[1]   Nucleophilic transition metal based cyclization of allenes [J].
Bates, RW ;
Satcharoen, V .
CHEMICAL SOCIETY REVIEWS, 2002, 31 (01) :12-21
[2]   FUNCTIONAL ANALOGS OF CC-1065 AND THE DUOCARMYCINS INCORPORATING THE 9A-(CHLOROMETHYL)-1,2,9,9A-TETRAHYDROCYCLOPROPA[C]BENZ[E]INDOL-4-ONE (C2BI) ALKYLATION SUBUNIT - SYNTHESIS AND PRELIMINARY DNA ALKYLATION STUDIES [J].
BOGER, DL ;
PALANKI, MSS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (24) :9318-9327
[3]   Allenic compounds and isothiocyanates as key building units in the synthesis of heterocycles [J].
Brandsma, L ;
Nedolya, NA .
SYNTHESIS-STUTTGART, 2004, (05) :735-745
[4]   Synthesizing allenes today (1982-2006) [J].
Brummond, Kay M. ;
DeForrest, Jolie E. .
SYNTHESIS-STUTTGART, 2007, (06) :795-818
[5]   Efficient Synthesis of 3-Chloromethyl-2(5H)-furanones and 3-Chloromethyl-5,6-dihydropyran-2-ones via the PdCl2-Catalyzed Chlorocyclocarbonylation of 2,3-or 3,4-Allenols [J].
Cheng, Xin ;
Jiang, Xuefeng ;
Yu, Yihua ;
Ma, Shengming .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (22) :8960-8965
[6]   EFFICIENT HOMOLOGATION OF ACETYLENES TO ALLENES [J].
CRABBE, P ;
FILLION, H ;
ANDRE, D ;
LUCHE, JL .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (19) :859-860
[7]  
CRABBE P, 1979, TETRAHEDRON LETT, P893
[8]   SYNTHETIC USE OF AN UNUSUAL ORGANOCUPRATE INTERMEDIATE [J].
DOLLAT, JM ;
LUCHE, JL ;
CRABBE, P .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1977, (21) :761-762
[9]  
Hashmi ASK, 2000, ANGEW CHEM INT EDIT, V39, P3590
[10]   C-C-bond formation by the palladium-catalyzed cycloisomerization/dimerization of terminal allenyl ketones: Selectivity and mechanistic aspects [J].
Hashmi, ASK ;
Ruppert, TL ;
Knofel, T ;
Bats, JW .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (21) :7295-7304