Categories: C-S Bond Formation >
Synthesis of propargylic sulfides
A general and efficient FeCl3-catalyzed substitution reaction of propargylic alcohols with carbon- and heteroatom-centered nucleophiles such as allyl trimethylsilane, alcohols, aromatic compounds, thiols, and amides, forms new C-C, C-O, C-S and C-N bonds.
Z.-P. Zhan, J.-L. Yu, Y.-Y. Cui, R.-F. Yang, W.-Z. Yang, J.-P. Li, J. Org. Chem., 2006, 71, 8298-8301.
An economic and practical transformation from secondary alkyl-substituted propargyl acetates to a variety of nucleophilic substitution products is catalyzed by inexpensive InCl3. High yields and excellent chemoselectivity were obtained. Five-, six-, and seven-membered propargyl cycloethers were also successfully constructed.
M. Lin, L. Hao, X.-t. Liu, Q.-z. Chen, F. Wu, P. Yan, S.-x. Xu, X.-l. Chen, J.-j. Wen, Z.-p. Zhan, Synlett, 2011, 665-670.
A ruthenium-catalyzed S-propargylation of thiols by propargylic carbonates under neutral conditions, in which specific requirements inherent to the different reactivities of aliphatic and aromatic thiols was achieved by tuning both the nature of the ligands and the experimental conditions.
T. Kondo, Y. Kanda, A. Baba, K. Fukuda, A. Nakamura, K. Wada, Y. Morisaki, T.-A. Mitsudo, J. Am. Chem. Soc., 2002, 124, 12960-12961.