Zinc(II)-catalyzed redox cross-dehydrogenative coupling of propargylic amines and terminal alkynes for synthesis of N-tethered 1,6-enynes.
作者： Tsuyuka Sugiishi , Hiroyuki Nakamura
DOI: 10.1021/JA211092Q
关键词:
摘要: The zinc(II)-catalyzed redox cross-dehydrogenative coupling (CDC) of propargylic amines and terminal alkynes proceeds to afford N-tethered 1,6-enynes. In the current CDC reaction, a C(sp)–C(sp3) bond is formed between carbon adjacent nitrogen atom in amine alkyne with reduction C–C triple amine, which acts as an internal oxidant.
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Tsuyuka Sugiishi, Akifumi Kimura, Hiroyuki Nakamura, Copper(I)-Catalyzed Substitution Reactions of Propargylic Amines: Importance of C(sp)−C(sp3) Bond Cleavage in Generation of Iminium Intermediates Journal of the American Chemical Society. ,vol. 132, pp. 5332- 5333 ,(2010) , 10.1021/JA9109055
Corinne Aubert, Olivier Buisine, Max Malacria, The behavior of 1,n-enynes in the presence of transition metals. Chemical Reviews. ,vol. 102, pp. 813- 834 ,(2002) , 10.1021/CR980054F
Mathias Schelwies, Adrian L. Dempwolff, Frank Rominger, Günter Helmchen, Gold-catalyzed intermolecular addition of carbonyl compounds to 1,6-enynes. Angewandte Chemie. ,vol. 46, pp. 5598- 5601 ,(2007) , 10.1002/ANIE.200701378
Chao-Jun Li, Cross-dehydrogenative coupling (CDC): exploring C-C bond formations beyond functional group transformations. Accounts of Chemical Research. ,vol. 42, pp. 335- 344 ,(2009) , 10.1021/AR800164N
Delphine Brissy, Myriem Skander, Hélène Jullien, Pascal Retailleau, Angela Marinetti, Platinum(II) catalysts for highly enantioselective 1,6-enyne cycloisomerizations. synthetic, structural, and catalytic studies. Organic Letters. ,vol. 11, pp. 2137- 2139 ,(2009) , 10.1021/OL900724Z
Irina Jovel, Saisuree Prateeptongkum, Ralf Jackstell, Nadine Vogl, Christoph Weckbecker, Matthias Beller, α-Functionalization of non-activated aliphatic amines: ruthenium-catalyzed alkynylations and alkylations Chemical Communications. ,vol. 46, pp. 1956- 1958 ,(2010) , 10.1039/B924674F
Z. Li, D. S. Bohle, C.-J. Li, Cu-catalyzed cross-dehydrogenative coupling: A versatile strategy for C–C bond formations via the oxidative activation of sp3 C–H bonds Proceedings of the National Academy of Sciences of the United States of America. ,vol. 103, pp. 8928- 8933 ,(2006) , 10.1073/PNAS.0601687103
Allison G. Condie, José C. González-Gómez, Corey R. J. Stephenson, Visible-light photoredox catalysis: aza-Henry reactions via C-H functionalization. Journal of the American Chemical Society. ,vol. 132, pp. 1464- 1465 ,(2010) , 10.1021/JA909145Y
D. E. Frantz, R. Fässler, C. S. Tomooka, E. M. Carreira, The Discovery of Novel Reactivity in the Development of C−C Bond-Forming Reactions: In Situ Generation of Zinc Acetylides with ZnII/R3N Accounts of Chemical Research. ,vol. 33, pp. 373- 381 ,(2000) , 10.1021/AR990078O
Zhiping Li, Chao-Jun Li, CuBr-catalyzed efficient alkynylation of sp3 C-H bonds adjacent to a nitrogen atom. Journal of the American Chemical Society. ,vol. 126, pp. 11810- 11811 ,(2004) , 10.1021/JA0460763