131558-77-5Relevant articles and documents
Highly Regio and Stereoselective Intermolecular Seleno- and Thioamination of Alkynes
Zheng, Guangfan,Zhao, Jinbo,Li, Zhanyu,Zhang, Qiao,Sun, Jiaqiong,Sun, Haizhu,Zhang, Qian
, p. 3513 - 3518 (2016)
By using N-fluorobenzenesulfonimide as both the oxidant and the amination reagent, we have realized the first example of the intermolecular chalcogenative amination of alkynes, which grants facile, highly regio- and stereoselective access to chalcogenated enamides. The reaction features mild conditions, high yields and selectivities, remarkably broad substrate scope, and excellent functional group tolerance. Mechanistic studies indicate the in situ generated chalcogen imidates to be the actual reactive species, which in turn, has clarified the mechanism of related transformations. These reactions represent significant additions to the development of the highly selective amino bisfunctionalization of alkynes.
Water-soluble polymer-bound, recoverable palladium(0)-phosphine catalysts
Bergbreiter, David E.,Liu, Yun-Shan
, p. 7843 - 7846 (1997)
The synthesis of a water-soluble polymer-bound Pd(0)-phosphine catalyst is described. This soluble polymeric catalyst is soluble in aqueous or mixed aqueous/organic media and has high activity in nucleophilic allylic substitution and in sp-sp2 coupling reactions of aryl iodides with terminal alkynes. The catalyst can be recycled efficiently by solvent or thermal precipitation methods.
Carbamoyl-Substituted N-Heterocyclic Carbene Complexes of Palladium(II): Application to Sonogashira Cross-Coupling Reactions
Batey, Robert A.,Shen, Ming,Lough, Alan J.
, p. 1411 - 1414 (2002)
(matrix presented) The first examples of N-carbamoyl-substituted heterocyclic carbene Pd(II) complexes are described. These thermal and hydrolytically stable complexes are readily prepared from carbamoyl imidazolium salts and efficiently promote Sonogashi
Enantioselective Ni/N-Heterocyclic Carbene-Catalyzed Redox-Economical Coupling of Aldehydes, Alkynes, and Enones for Rapid Construction of Acyclic All-Carbon Quaternary Stereocenters
Chen, Guang,Shi, Shi-Liang,Zhang, Wu-Bin
supporting information, (2022/01/08)
Acyclic quaternary carbon stereocenters exist widely in natural products and bioactive molecules, but their enantioselective construction remains a prominent challenge. In particular, multicomponent enantioselective couplings of simple precursors to acyclic all-carbon quaternary stereocenters are very rare. We describe herein an N-heterocyclic carbene (NHC)-Ni catalyzed redox-economical three-component reaction of aldehydes, alkynes, and enones that proceeds in a highly chemo-, regio-, and enantioselective manner. A wide variety of valuable acyclic α-quaternary chiral ketones were synthesized in a single step with 100% atom economy. This reaction proceeds through the formation of a transient cyclic enolate followed by an aldol reaction/ring-opening sequence. The strategy is expected to inspire new and efficient approaches to generate other acyclic quaternary stereocenters.
Sodium-metal-promoted reductive 1,2-syn-diboration of alkynes with reduction-resistant trimethoxyborane
Fukazawa, Mizuki,Ito, Shiori,Nogi, Keisuke,Takahashi, Fumiya,Yorimitsu, Hideki
, p. 1171 - 1179 (2020/10/18)
Reductive 1,2-diboration of alkynes has been accomplished by means of sodium dispersion in the presence of trimethoxyborane as a reduction-resistant boron electrophile. Two boron moieties can be introduced onto alkynes with excellent syn selectivity to afford the corresponding (Z)-1,2-diborylalkenes. Bis(borate) species generated in situ can be involved in one-pot Suzuki-Miyaura arylation, formal arylboration of alkynes thus being executed.
C-H alkenylation/cyclization and sulfamidation of 2-phenylisatogens using: N -oxide as a directing group
Guo, Lingmei,Tang, Baolan,Nie, Ruifang,Liu, Yanzhao,Lv, Shan,Wang, Huijing,Guo, Li,Hai, Li,Wu, Yong
supporting information, p. 10623 - 10626 (2019/09/06)
The first example of transition-metal-catalyzed C-H activations of 2-phenylisatogens with alkynes and sulfonyl azides has been developed using N-oxide as the directing group. Ru(ii)-Catalyzed C-H alkenylation/cyclization and Ir(iii)-catalyzed direct C-H sulfamidation proceeded with good yields and excellent functional group tolerance. Importantly, these two transformations provided straightforward routes for the synthesis of indol-3-one derivatives and sulfamidated 2-phenylisatogens respectively, which might be of considerable bioactivities.
