Iridium-Catalyzed Addition of Acid Chlorides to Terminal Alkynes
作者： Tomohiro Iwai , Tetsuaki Fujihara , Jun Terao , Yasushi Tsuji
DOI: 10.1021/JA901778Y
关键词:
摘要: An iridium N-heterocyclic carbene (NHC) complex, IrCl(cod)(IPr), successfully catalyzed an addition of common aromatic acid chlorides to terminal alkynes afford (Z)-β-chloro-α,β-unsaturated ketones regio- and stereoselectively. When the NHC ligand (IPr) was changed a phosphine (RuPhos), occurred with decarbonylation give corresponding (Z)-vinyl chlorides. Furthermore, former reaction using IrCl(cod)(IPr) can be applied catalytic synthesis 2,5-disubstituted furans.
acs.org
core.ac.uk
sci-hub.se 参考文章(19)
Taigo Kashiwabara, Kyoko Kataoka, Ruimao Hua, Shigeru Shimada, Masato Tanaka, CO-retentive addition reactions of fluorinated acid chlorides to alkynes. Organic Letters. ,vol. 7, pp. 2241- 2244 ,(2005) , 10.1021/OL050632W
H. Martens, F. Janssens, G. Hoornaert, Stereochemistry and mechanism of acylation of acetylenes Tetrahedron. ,vol. 31, pp. 177- 183 ,(1975) , 10.1016/0040-4020(75)85014-9
Ruben Martin, Stephen L. Buchwald, Palladium-Catalyzed Suzuki-Miyaura Cross-coupling Reactions Employing Dialkylbiaryl Phosphine Ligands Accounts of Chemical Research. ,vol. 41, pp. 1461- 1473 ,(2008) , 10.1021/AR800036S
Tomohiro Iwai, Tetsuaki Fujihara, Yasushi Tsuji, The iridium-catalyzed decarbonylation of aldehydes under mild conditions Chemical Communications. pp. 6215- 6217 ,(2008) , 10.1039/B813171F
Alexander S. Dudnik, Anna W. Sromek, Marina Rubina, Joseph T. Kim, Alexander V. Kel'i, Vladimir Gevorgyan, Metal-Catalyzed 1,2-Shift of Diverse Migrating Groups in Allenyl Systems as a New Paradigm toward Densely Functionalized Heterocycles Journal of the American Chemical Society. ,vol. 130, pp. 1440- 1452 ,(2008) , 10.1021/JA0773507
Xiaodan Zhao, Zhengkun Yu, Rhodium-Catalyzed Regioselective C−H Functionalization via Decarbonylation of Acid Chlorides and C−H Bond Activation under Phosphine-Free Conditions Journal of the American Chemical Society. ,vol. 130, pp. 8136- 8137 ,(2008) , 10.1021/JA803154H
Roy A. Kelly III, Hervé Clavier, Simona Giudice, Natalie M. Scott, Edwin D. Stevens, Jon Bordner, Ivan Samardjiev, Carl D. Hoff, Luigi Cavallo, Steven P. Nolan, Determination of N-Heterocyclic Carbene (NHC) Steric and Electronic Parameters using the [(NHC)Ir(CO)2Cl] System Organometallics. ,vol. 27, pp. 202- 210 ,(2008) , 10.1021/OM701001G
D. Milstein, J. K. Stille, A general, selective, and facile method for ketone synthesis from acid chlorides and organotin compounds catalyzed by palladium Journal of the American Chemical Society. ,vol. 100, pp. 3636- 3638 ,(1978) , 10.1021/JA00479A077
Ruimao Hua, Shun-ya Onozawa, Masato Tanaka, Rhodium-catalyzed nondecarbonylative addition reaction of ClCOCOOC2H5 to alkynes. Chemistry: A European Journal. ,vol. 11, pp. 3621- 3630 ,(2005) , 10.1002/CHEM.200401279
Toru Sugihara, Tetsuya Satoh, Masahiro Miura, Masakatsu Nomura, Rhodium-Catalyzed Mizoroki–Heck-Type Arylation of Alkenes with Aroyl Chlorides under Phosphane- and Base-Free Conditions Angewandte Chemie International Edition. ,vol. 42, pp. 4672- 4674 ,(2003) , 10.1002/ANIE.200351905