108972-13-0Relevant academic research and scientific papers
Decarboxylative Cross-Electrophile Coupling of N-Hydroxyphthalimide Esters with Aryl Iodides
Huihui, Kierra M. M.,Caputo, Jill A.,Melchor, Zulema,Olivares, Astrid M.,Spiewak, Amanda M.,Johnson, Keywan A.,Dibenedetto, Tarah A.,Kim, Seoyoung,Ackerman, Laura K. G.,Weix, Daniel J.
, p. 5016 - 5019 (2016)
A new method for the decarboxylative coupling of alkyl N-hydroxyphthalimide esters (NHP esters) with aryl iodides is presented. In contrast to previous studies that form alkyl radicals from carboxylic acid derivatives, no photocatalyst, light, or arylmetal reagent is needed, only nickel and a reducing agent (Zn). Methyl, primary, and secondary alkyl groups can all be coupled in good yield (77% ave yield). One coupling with an acid chloride is also presented. Stoichiometric reactions of (dtbbpy)Ni(2-tolyl)I with an NHP ester show for the first time that arylnickel(II) complexes can directly react with NHP esters to form alkylated arenes.
Ketones from Nickel-Catalyzed Decarboxylative, Non-Symmetric Cross-Electrophile Coupling of Carboxylic Acid Esters
Wang, Jiang,Cary, Brian P.,Beyer, Peyton D.,Gellman, Samuel H.,Weix, Daniel J.
, p. 12081 - 12085 (2019/08/12)
Synthesis of the C?C bonds of ketones relies upon one high-availability reagent (carboxylic acids) and one low-availability reagent (organometallic reagents or alkyl iodides). We demonstrate here a ketone synthesis that couples two different carboxylic acid esters, N-hydroxyphthalimide esters and S-2-pyridyl thioesters, to form aryl alkyl and dialkyl ketones in high yields. The keys to this approach are the use of a nickel catalyst with an electron-poor bipyridine or terpyridine ligand, a THF/DMA mixed solvent system, and ZnCl2 to enhance the reactivity of the NHP ester. The resulting reaction can be used to form ketones that have previously been difficult to access, such as hindered tertiary/tertiary ketones with strained rings and ketones with α-heteroatoms. The conditions can be employed in the coupling of complex fragments, including a 20-mer peptide fragment analog of Exendin(9–39) on solid support.
Ruthenium-catalyzed three-component coupling via hydrative conjugate addition of alkynes to alkenes: One-pot synthesis of 1,4-dicarbonyl compounds
Chen, Yiyun,Park, Sung Hwan,Lee, Chung Whan,Lee, Chulbom
supporting information; experimental part, p. 2000 - 2004 (2011/11/07)
A catalytic three-way rendezvous: Terminal alkynes undergo metal vinylidene formation, anti-Markovnikov hydration to give a metal acyl complex, and conjugate addition to produce synthetically useful 1,4-dicarbonyl compounds under ruthenium catalysis. This one-pot three-component coupling reaction is a useful platform for further exploration in alkyne functionalization.
Modular approach to saturated and α,β-unsaturated ketones
Debien, Laurent,Quiclet-Sire, Beatrice,Zard, Samir Z.
supporting information; experimental part, p. 5676 - 5679 (2011/12/15)
2-Fluoro-6-pyridinyloxy derivatives of 2-ethoxyvinyl carbinols react with radicals derived from xanthates by an addition-fragmentation pathway to give highly functionalized ketones after acid hydrolysis. 1,4-Diketones are readily accessible by this approa
