Preparation of conjugated 1,3-enynes by Rh(III)-catalysed alkynylation of alkenes via C-H activation

被引:163
作者
Collins, Karl D. [1 ]
Lied, Fabian [1 ]
Glorius, Frank [1 ]
机构
[1] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany
基金
欧洲研究理事会;
关键词
CATALYZED DIRECT ALKYNYLATION; ROBUSTNESS SCREEN; RAPID ASSESSMENT; GOLD; ALKYNES; CYCLOISOMERIZATION; BONDS; EBX; FUNCTIONALIZATION; ETHYNYLATION;
D O I
10.1039/c4cc01141d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An experimentally simple additive-free Rh(III)-catalysed direct alkynylation of alkenes has been developed. This protocol employs commercially available TIPS-EBX as the alkyne source, giving access to conjugated terminal enynes following a simple silyl-deprotection. This method has also been applied to arenes.
引用
收藏
页码:4459 / 4461
页数:3
相关论文
共 77 条
[1]   Carboxylate-Assisted Ruthenium-Catalyzed Alkyne Annulations by C-H/Het-H Bond Functionalizations [J].
Ackermann, Lutz .
ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (02) :281-295
[2]   Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].
Ackermann, Lutz .
CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345
[3]   Ruthenium-Catalyzed Direct ortho-Alkynylation of Arenes with Chelation Assistance [J].
Ano, Yusuke ;
Tobisu, Mamoru ;
Chatani, Naoto .
SYNLETT, 2012, (19) :2763-2767
[4]   The behavior of 1,n-enynes in the presence of transition metals [J].
Aubert, C ;
Buisine, O ;
Malacria, M .
CHEMICAL REVIEWS, 2002, 102 (03) :813-834
[5]   Benziodoxole-based hypervalent iodine reagents for atom-transfer reactions [J].
Brand, Jonathan P. ;
Gonzalez, Davinia Fernandez ;
Nicolai, Stefano ;
Waser, Jerome .
CHEMICAL COMMUNICATIONS, 2011, 47 (01) :102-115
[6]   Electrophilic alkynylation: the dark side of acetylene chemistry [J].
Brand, Jonathan P. ;
Waser, Jerome .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (11) :4165-4179
[7]   Para-Selective Gold-Catalyzed Direct Alkynylation of Anilines [J].
Brand, Jonathan P. ;
Waser, Jerome .
ORGANIC LETTERS, 2012, 14 (03) :744-747
[8]   One-pot gold-catalyzed synthesis of 3-silylethynyl indoles from unprotected o-alkynylanilines [J].
Brand, Jonathan P. ;
Chevalley, Clara ;
Waser, Jerome .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2011, 7 :565-569
[9]   Direct Alkynylation of Thiophenes: Cooperative Activation of TIPS-EBX with Gold and Bronsted Acids [J].
Brand, Jonathan P. ;
Waser, Jerome .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (40) :7304-7307
[10]   Direct Alkynylation of Indole and Pyrrole Heterocycles [J].
Brand, Jonathan P. ;
Charpentier, Julie ;
Waser, Jerome .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (49) :9346-9349