410094-59-6Relevant academic research and scientific papers
Rhodium-Catalyzed Deoxygenation and Borylation of Ketones: A Combined Experimental and Theoretical Investigation
Tao, Lei,Guo, Xueying,Li, Jie,Li, Ruoling,Lin, Zhenyang,Zhao, Wanxiang
, p. 18118 - 18127 (2020/11/26)
The rhodium-catalyzed deoxygenation and borylation of ketones with B2pin2 have been developed, leading to efficient formation of alkenes, vinylboronates, and vinyldiboronates. These reactions feature mild reaction conditions, a broad substrate scope, and excellent functional-group compatibility. Mechanistic studies support that the ketones initially undergo a Rh-catalyzed deoxygenation to give alkenes via boron enolate intermediates, and the subsequent Rh-catalyzed dehydrogenative borylation of alkenes leads to the formation of vinylboronates and diboration products, which is also supported by density functional theory calculations.
Stereoselective Synthesis of Vinyl Iodides through Copper(I)-Catalyzed Finkelstein-Type Halide-Exchange Reaction
Feng, Xiujuan,Zhang, Haixia,Lu, Wenbo,Yamamoto, Yoshinori,Almansour, Abdulrahman I.,Arumugam, Natarajan,Kumar, Raju Suresh,Bao, Ming
, p. 2727 - 2732 (2017/06/13)
An efficient method for the stereoselective synthesis of vinyl iodides is described. The reactions of vinyl bromides with potassium iodide proceed smoothly in the presence of a copper catalyst under mild reaction conditions to produce the corresponding vinyl iodides stereospecifically and in satisfactory to excellent yields.
Ruthenium-catalyzed one-pot synthesis of (E)-(2-arylvinyl)boronates through an isomerization/cross-metathesis sequence from allyl-substituted aromatics
Hemelaere, Remy,Caijo, Frederic,Mauduit, Marc,Carreaux, Francois,Carboni, Bertrand
supporting information, p. 3328 - 3333 (2014/06/09)
We described the efficient preparation of (E)-(2-arylvinyl)boronates from allylbenzene derivatives on the basis of an isomerization/cross-metathesis sequence catalyzed by a modified Hoveyda-Grubbs catalyst. The implementation of the experimental procedure was simple and compatible with a large variety of substrates. This methodology provides a new chemical transformation not described to date. Allyl-substituted aromatics can thus be converted into diversely functionalized compounds, such as (E)-stilbene derivatives or (E)-vinyl azides, in only two steps. Copyright
Synthesis of 2- and 2,3-substituted Pyrazolo[1,5- a ]pyridines: Scope and mechanistic considerations of a domino direct alkynylation and cyclization of n -iminopyridinium ylides using alkenyl bromides, alkenyl iodides, and alkynes
Mousseau, James J.,Bull, James A.,Ladd, Carolyn L.,Fortier, Angelique,Sustac Roman, Daniela,Charette, Andre B.
experimental part, p. 8243 - 8261 (2012/01/03)
Direct functionalization and tandem processes have both received considerable recent interest due to their cost and time efficiency. Herein we report the synthesis of difficult to obtain 2-substituted pyrazolo[1,5-a] pyridines through a tandem palladium-catalyzed/silver-mediated elimination/direct functionalization/cyclization reaction involving N-benzoyliminopyridinium ylides. As such, these biologically important molecules are prepared in an efficient, high-yielding manner, only requiring a two-step sequence from pyridine. Aryl-substituted alkenyl bromides and iodides are effective ylide coupling partners. Mechanistic studies led to the use of terminal alkynes, which extended the scope of the reaction to include alkyl substitution on the unsaturated reactive site. The optimization, scope, and mechanistic considerations of the process are discussed.
Copper-catalyzed direct alkenylation of N-iminopyridinium ylides
Mousseau, James J.,Bull, James A.,Charette, Andre B.
supporting information; experimental part, p. 1115 - 1118 (2010/05/17)
(Figure Presented) A versatile Cu-catalyzed direct C-H alkenylation of N-iminopyridinium ylides, compatible with several different copper sources (including a penny), provides a powerful and inexpensive method for the synthesis of functionalized pyridine derivatives. Chemoselective functionalization of halide-containing compounds allows the synthesis of alkenyl pyridines containing reactive tethers for further functionalization
Recyclable nano copper oxide catalyzed stereoselective synthesis of vinyl sulfides under ligand-free conditions
Reddy, Vutukuri Prakash,Swapna, Kokkirala,Kumar, Akkilagunta Vijay,Rao, Kakulapati Rama
experimental part, p. 2783 - 2788 (2010/03/03)
A simple and efficient protocol for the cross-coupling of vinyl halides with thiols catalyzed by recyclable CuO nanoparticles under ligand-free conditions is reported. This methodology results in the synthesis of a variety of vinyl sulfides in excellent y
New one-pot synthesis of (E)-β-aryl vinyl halides from styrenes
Pawluc, Piotr,Hreczycho, Grzegorz,Szudkowska, Justyna,Kubicki, Maciej,Marciniec, Bogdan
supporting information; experimental part, p. 3390 - 3393 (2009/12/01)
A new, efficient protocol for the highly stereoselective one-pot synthesis of (E)-β-aryl vinyl iodides and (￡)-β-aryl vinyl bromides from styrenes based on sequential ruthenium-catalyzed silylative coupling-N-halosuccinimide-mediated halodesilylation reactions is reported.
Convenient one-pot synthesis of (E)-β-aryl vinyl halides from benzyl bromides and dihalomethanes
Bull, James A.,Mousseau, James J.,Charette, Andre B.
supporting information; experimental part, p. 5484 - 5488 (2009/06/06)
(Chemical Equation Presented) (E)-β-Aryl vinyl iodides are synthesized in high yield with excellent stereoselectivity from benzyl bromides by a one-pot homologation/ stereoselective elimination procedure. Convenient conditions involving the anion of diiodomethane and an excess of base provide complete consumption of the benzyl bromide and elimination from a diiodoalkane intermediate. Similar conditions provide (E)-β-aryl vinyl chlorides and bromides by employing the anions of ICH2CI or CH2Br 2. The functional group tolerance and facile purification allows rapid access to a wide range of functionalized vinyl halides.
