353261-75-3Relevant academic research and scientific papers
Palladium-Catalyzed Allylic Amidation with N-Heterocycles via sp3 C-H Oxidation
Cook, Gregory R.,Kumar, Dinesh,Vemula, Sandeep R.
, p. 5295 - 5301 (2016)
An atom-economic direct intermolecular allylic amidation of electron-deficient tautomerizable N-heterocycles is reported via allylic C-H activation of terminal olefins with a PdCl2 catalyst. The reaction did not require any activators (base or Lewis acid) or external ligands and proceeded with high chemo- (N vs O), regio- (linear vs branched), and stereoselectivity (E vs Z) for a variety of N-heterocycles and terminal olefins. Mechanistic investigation and stoichiometric studies validate the sulfoxide-ligand-assisted allylic C-H bond cleavage to form a π-allylpalladium intermediate in the reaction pathway. Excellent selectivity was observed during intermolecular competition demonstrating the differential nucleophilicity of N-heterocycles and differential susceptibility of allyl C-H bond cleavage to form π-allylpalladium complexes directly from terminal olefins.
Insights into Substrate Self-Assisted Activation of Allylic Alcohols Guiding to Mild Allylic Substitution of Tautomerizable Heteroarenes
Cao, Xinhua,Huang, Lijun,Liu, Aoqi,Ma, Bing,Ma, Xiantao,Yu, Jing,Zheng, Lingyun,Zhou, Qiuju
, p. 5097 - 5103 (2020/05/01)
A substrate self-assisted activation of allylic alcohols by tautomerizable heteroarenes via hydrogen bonding was disclosed by various NMR techniques, including variable-temperature 1H NMR, Job plot, and 1H NMR titration. Guided by th
Palladium-catalyzed allylation of tautomerizable heterocycles with alkynes
Lu, Chuan-Jun,Chen, Dong-Kai,Chen, Hong,Wang, Hong,Jin, Hongwei,Huang, Xifu,Gao, Jianrong
, p. 5756 - 5763 (2017/07/22)
A method for the allylic amidation of tautomerizable heterocycles was developed by a palladium catalyzed allylation reaction with 100% atom economy. A series of structurally diverse N-allylic substituted heterocycles can be synthesized in good yields with high chemo-, regio-, and stereoselectivities under mild conditions.
Highly chemo- and regioselective allylic substitution with tautomerizable heteroarenes
Kumar, Dinesh,Vemula, Sandeep R.,Cook, Gregory R.
, p. 4300 - 4306 (2015/08/11)
Tautomerizable heteroarenes, bearing multiple interconvertible nucleophilic centers exhibit high chemo- and regioselective allylation irrespective of allylating agents used under Pd-catalysis. The achieved selectivity may be attributed to the dominant lactam form of heteroarenes and Pd-catalyzed intramolecular allylic substitution. A generalized green protocol for chemo- and regioselective allylation of biologically relevant heteroarenes with allyl alcohols in dimethyl carbonate (DMC) as solvent was developed. Excellent selectivity was observed during intermolecular competition study demonstrating the differential nucleophilicity of tautomerizable heteroarenes and differential allyl palladium forming ability of a variety of allyl alcohols.
Synthesis of heteroarenes using cascade radical cyclisation via iminyl radicals
Bowman, W. Russell,Cloonan, Martin O.,Fletcher, Anthony J.,Stein, Tobias
, p. 1460 - 1467 (2007/10/03)
Cascade radical cyclisation involving homolytic aromatic substitution has been used to synthesise new tetracycles. Treatment of vinyl iodide radical precursors with Me3Sn radicals (from hexamethylditin) yielded intermediate vinyl radicals which
