2699-89-0Relevant articles and documents
Ligand-Controlled Regiodivergence in the Copper-Catalyzed [2,3]- and [1,2]-Rearrangements of Iodonium Ylides
Xu, Bin,Tambar, Uttam K.
supporting information, p. 12073 - 12076 (2016/09/28)
Despite the importance of allylic ylide rearrangements for the synthesis of complex molecules, the catalyst control of [2,3]- and [1,2]-rearrangements remains an unsolved problem. We developed the first regiodivergent [2,3]- and [1,2]-rearrangements of iodonium ylides that are controlled by copper catalysts bearing different ligands. In the presence of a 2,2′-dipyridyl ligand, diazoesters and allylic iodides react via a [2,3]-rearrangement pathway. Alternatively, a phosphine ligand favors the formation of the [1,2]-rearrangement product. A series of α-iodoesters containing a broad range of functional groups were obtained in high yields, regioselectivities, and diastereoselectivities. Deuterium-labeling studies suggest distinct mechanisms for the regioselective rearrangements.
Catalytic asymmetric bromoetherification and desymmetrization of olefinic 1,3-diols with C2-symmetric sulfides
Ke, Zhihai,Tan, Chong Kiat,Chen, Feng,Yeung, Ying-Yeung
supporting information, p. 5627 - 5630 (2014/05/06)
An enantioselective and highly diastereoselective bromoetherification and desymmetrization of olefinic 1,3-diols has been developed using a C 2-symmetric cyclic sulfide catalyst. This methodology has been successfully applied to the synthesis of the key intermediate of an orally active antifungal drug posaconazole (Noxafil).
Exploratory studies on the reaction between iodoarenes and acetylenes: One-pot, Pd-[Bmim][BF4] catalyzed preparation of trianisylethylene
Barros, Jose C.,Souza, Andrea L. F.,Da Silva, Joaquim F. M.,Antunes
scheme or table, p. 549 - 553 (2012/01/13)
The reaction between iodoarenes and acetylenes mediated by palladium was studied, showing selectivity changes based on the nature of the substituent. A new, phosphine-, copper-, and amine-free methodology was developed, in which the synthesis of trianisylethylene from 4-iodoanisole and trimethylsilylacetylene was promoted presumably by an N-heterocyclic-carbene derived from an ionic liquid and a palladium salt, using ethanol as the hydrogen source. Graphical Abstract: [Figure not available: see fulltext.]