405872-51-7Relevant 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
supporting information, 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.
Cyclic Vinyl(aryl)iodonium Salts: Synthesis and Reactivity
Kepski, Konrad,Rice, Craig R.,Moran, Wesley J.
supporting information, p. 6936 - 6939 (2019/09/30)
A convenient, highly regioselective synthesis of five-membered cyclic vinyl(aryl)iodonium salts directly from β-iodostyrenes is presented. An X-ray crystal structure confirms the identity of these heterocycles. These λ3-iodanes can be converted
Stereospecific Iron-Catalyzed Carbon(sp2)-Carbon(sp3) Cross-Coupling with Alkyllithium and Alkenyl Iodides
Lu, Xiao-Lin,Shannon, Mark,Peng, Xiao-Shui,Wong, Henry N. C.
supporting information, p. 2546 - 2549 (2019/03/26)
An efficient synthetic protocol involving iron-catalyzed cross-coupling reactions between organolithium compounds and alkenyl iodides as key coupling partners was achieved. More than 30 examples were obtained with moderate to good yields and high stereospecificity. Gram-scale and synthetic applications of this procedure are recorded herein to demonstrate its feasibility and potential utilization.
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.
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.
