54090-91-4Relevant academic research and scientific papers
Visible light-induced C-C bond cleavage in a multicomponent reaction cascade allowing acylations of sulfoximines with ketones
Bolm, Carsten,Ma, Ding,Shi, Peng,Tu, Yongliang,Wang, Chenyang,Zhang, Duo
supporting information, p. 8096 - 8101 (2021/10/04)
Visible light induces C-C-bond cleavage reactions of ketones, which can be utilized forN-acylations of sulfoximines. No (photo)catalyst is required, and the reactions occur at ambient temperature in air. The substrate scope is broad for both ketones and sulfoximines. For convertingNH-sulfoximines, the presence of NBS is essential.
Microwave-Accelerated N-Acylation of Sulfoximines with Aldehydes under Catalyst-Free Conditions
Ambala, Srinivas,Arvidsson, Per I.,Govender, Thavendran,Kruger, Hendrik G.,Naicker, Tricia,Rajbongshi, Kamal K.
, p. 1279 - 1286 (2020/04/15)
An efficient catalyst-free radical cross-coupling reaction between aromatic aldehydes and sulfoximines was developed. The reaction took place in the presence of N-bromosuccinimide as the radical initiator under microwave irradiation to afford the corresponding acylated sulfoximines in moderate to excellent yields (27 examples). This protocol proved to be rapid, easy to handle, and applicable to a broad scope of substrates.
One-Pot Unsymmetrical {[4 + 2] and [4 + 2]} Double Annulations of o/ o′-C-H Bonds of Arenes: Access to Unusual Pyranoisoquinolines
Shankar, Majji,Ghosh, Koushik,Mukherjee, Kallol,Rit, Raja K.,Sahoo, Akhila K.
supporting information, p. 5144 - 5148 (2018/09/13)
With the aid of a transformable sulfoximine directing group, unprecedented one-pot unsymmetrical double annulations {[4 + 2] and [4 + 2]} of hetero(arenes) with alkynes are revealed under Ru(II) catalysis. Functionalization of both ortho-C-H bonds of (hetero)arene is reflected in the building of unusual 6,6-fused pyranoisoquinoline skeletons. Construction of four [(C-C)-(C-N) and (C-C)-(C-O)] bonds occurs in one step under single catalytic conditions. The challenging unsymmetrical double annulations of both o-C-H bonds of arenes with two distinct alkynes is effectively demonstrated. Control experiments and deuterium scrambling findings are shown.
Iron-Catalyzed One-Pot N-Aroylation of NH-Sulfoximines with Methylarenes through Benzylic C-H Bond Oxidation
Muneeswara, Madithedu,Kotha, Surya Srinivas,Sekar, Govindasamy
, p. 1541 - 1549 (2016/06/01)
An efficient catalytic method has been developed for the synthesis of N-aroylated sulfoximines from readily available toluenes (methylarenes) as source of the aroyl coupling partner and NH-sulfoximines, employing an environmentally benign iron catalyst. T
Palladium nanoparticles catalyzed aroylation of: NH -sulfoximines with aryl iodides
Sharma, Nidhi,Sekar, Govindasamy
, p. 37226 - 37235 (2016/05/24)
A novel approach towards aroylation of NH-sulfoximines using Pd nanoparticles stabilized by a binaphthyl backbone (Pd-BNP) has been developed. This synthetic protocol involves the Pd-BNP promoted carbon monoxide insertion of aryl iodides to form an aroyl intermediate which further reacts with NH-sulfoximines to form N-aroyl sulfoximine derivatives in good to excellent yields. The Pd-BNP catalyst was recovered and reused up to six times.
Iron-Catalyzed Acylative Dealkylation of N-Alkylsulfoximines
Lamers, Philip,Priebbenow, Daniel L.,Bolm, Carsten
, p. 5594 - 5602 (2015/09/01)
As a result of our recent investigations into the N-functionalization of sulfoximines, an iron-catalyzed dealkylative acylation of N-alkylsulfoximines has been developed. This process involves a Polonovski-type dealkylation of an N-alkylated sulfoximine to afford a reactive intermediate that is trapped in the presence of a suitable aldehyde or anhydride to afford N-acyl- and N-aroylsulfoximine derivatives in one pot. Subsequent cleavage of the acyl or aroyl group under acidic conditions generates a synthetically valuable NH-sulfoximine. The dealkylation of N-alkylsulfoximines has been developed utilizing TBHP as oxidant and a catalytic amount of iron chloride to furnish a range of N-acyl- and N-aroylsulfoximines. This method facilitates the use of N-alkyl protecting groups that provide very stable N-protected sulfoximine derivatives that can be readily modified at sites other than the nitrogen atom.
Sulfoximine-directed ruthenium-catalyzed ortho -C-H Alkenylation of (Hetero)Arenes: Synthesis of EP3 receptor antagonist analogue
Yadav, M. Ramu,Rit, Raja K.,Shankar, Majji,Sahoo, Akhila K.
, p. 6123 - 6134 (2014/07/21)
The reusable sulfoximine directing-group-assisted Ru(II)-catalyzed chemo- and regioselective ortho-C-H alkenylation of arenes and heteroarenes with acrylates and α,β-unsaturated ketones/vinyl sulfone is shown. The N-aroyl sulfoximine undergoes annulation with diphenylacetylene, delivering isoquinolinones and methyl phenyl sulfoxide. The present protocol is successfully employed for the synthesis of the EP3 receptor antagonist analogue.
Sulfoximines: A reusable directing group for chemo-and regioselective ortho C-H oxidation of arenes
Yadav, M. Ramu,Rit, Raja K.,Sahoo, Akhila K.
supporting information; experimental part, p. 5541 - 5545 (2012/06/01)
Sulfoximines direct: A new protocol for the chemo-and regioselective ortho C-H acetoxylation of arenes in N-benzoylated sulfoximines is reported. The sulfoximine directing group is easily detached from the C-H oxidation product through acid-promoted hydrolysis, isolated, and reused (see scheme). The meta-substituted phenols are synthesized following this strategy and the stereointegrity of the sulfoximine is preserved in this transformation. C(sp3)-H acetoxylation of the methyl group is also demonstrated.
