72046-73-2Relevant articles and documents
Development of Transition-Metal-Free Lewis Acid-Initiated Double Arylation of Aldehyde: A Facile Approach Towards the Total Synthesis of Anti-Breast-Cancer Agent
Singh, Sanjay,Mahato, Rina,Sharma, Pragya,Yadav, Naveen,Vodnala, Nagaraju,Kumar Hazra, Chinmoy
supporting information, (2022/02/19)
This work describes a mild and robust double hydroarylation strategy for the synthesis of symmetrical /unsymmetrical diaryl- and triarylmethanes in excellent yields using Lambert salt (0.2–1.0 mol%). Despite the anticipated challenges associated with controlling selective product formation, unsymmetrical diaryl- and triarylmethanes products are obtained unprecedentedly. A highly efficient gram scale reaction has also been reported (TON for symmetrical product=475 and for unsymmetrical product=390). The synthetic utility of the methodology is demonstrated by the preparation of several unexplored diaryl- and triarylmethane-based biologically relevant molecules, such as arundine, vibrindole A, turbomycin B, and certain anti-inflammatory agents. A total synthesis of an anti-breast-cancer agent is also demonstrated. Control experiments, Hammett analysis, HRMS and GC-MS studies reveal the reaction intermediates and reaction mechanism.
Polyethylene Glycol (PEG-400) as Methylene Spacer and Green Solvent for the Synthesis of Heterodiarylmethanes under Metal-Free Conditions
Kumar, Rahul,Rawat, Deepa,Adimurthy, Subbarayappa
supporting information, p. 3499 - 3507 (2020/05/16)
Polyethylene glycol 400 (PEG-400) has been employed as a green, biodegradable solvent as well as methylene spacer for the one-pot synthesis of heterodiarylmethanes under metal-free conditions. PEG-400 is used for the dimerization of both symmetrical and unsymmetrical fused heterocycles and arenes as methylene spacer. The reaction was facilitated by (diacetoxyiodo)benzene (PIDA) as an oxidant. This reaction proceeds without transition metal, base, ligand, and under additive-free conditions involving the coupling of sp3 and sp2-hybridized carbon atoms. The method is applicable for variety of heterocycles such as imidazopyridines, imidazothioazoles, imidazobenzothiozoles, indolizines, indole, 1-methyl-1H-indole, N,N-dimethylaniline and trimethoxybenzene. Good to excellent yields and applicability to gram-scale synthesis demonstrate the potential scope of the process for commercial/industrial applications.
Ammonium persulfate activated DMSO as a one-carbon synthon for the synthesis of methylenebisamides and other applications
Mahajan, Pankaj S.,Tanpure, Subhash D.,More, Namita A.,Gajbhiye, Jayant M.,Mhaske, Santosh B.
, p. 101641 - 101646 (2015/12/08)
Activation of DMSO to work as an economical and environmentally benign one-carbon synthon has been achieved by using a bench-top reagent ammonium persulfate for general and efficient access to symmetrical methylenebisamides from primary amides. This methodology was used to achieve a three-component Mannich reaction using acetophenone, saccharin and DMSO to furnish a β-amino ketone. It also provided a metal-free synthesis of thiadiazole and bis(phenyl)methane. Effectively, this method uses DMSO as a safer surrogate to formaldehyde. A mechanism for methylenebisamide formation involving radical intermediates has been proposed based on mechanistic studies.
