28295-59-2Relevant academic research and scientific papers
Synthesis of chiral benzyl alkyl sulfoxides by cyclohexanone monoxygenase from Acinetobacter NCIB 9871
Pasta,Carrea,Holland,Dallavalle
, p. 933 - 936 (1995)
Benzyl alkyl sulfides with alkyl groups from methyl to hexyl, para-alkylbenzyl groups from methyl to butyl, 2-phenylethyl methyl sulfide and 3-phenylpropyl methyl sulfide have been oxidized by cyclohexanone monooxygenase from Acinetobacter NCIB 9871. Sulf
Photochemistry of Tris(2,4-dibromophenyl)amine and its Application to Co-oxidation on Sulfides and Phosphines?
Bonesi, Sergio M.,Mella, Mariella,Merli, Daniele,Protti, Stefano
, p. 1278 - 1288 (2021/03/16)
The photochemistry of tris(2,4-dibromophenyl)amine was investigated via time-resolved nanosecond spectroscopy. The tris(2,4-dibromophenyl)amine radical cation (“Magic Green”) was immediately detected after the laser pulse; this intermediate then cyclizes to N-aryl-4a,4b-dihydrocarbazole radical cation. The latter transient reacted with molecular oxygen to provide the corresponding hydroperoxyl radical, which smoothly co-oxidize sulfides into sulfoxides. On the other hand, the photogenerated “Magic Green” was exploited to promote the co-oxidation of nucleophilic triarylphosphines to triarylphosphine oxides through an electron transfer process preventing the amine cyclization. In this case, the intermediate Ar3POO?+ was found to play a key role in phosphine oxide formation.
Chemoenzymatic Deracemization of Chiral Sulfoxides
Nosek, Vladimír,Mí?ek, Ji?í
supporting information, p. 9849 - 9852 (2018/07/31)
The highly enantioselective enzyme methionine sulfoxide reductase A was combined with an oxaziridine-type oxidant in a biphasic setup for the deracemization of chiral sulfoxides. Remarkably, high ee values were observed with a wide range of substrates, thus providing a practical route for the synthesis of enantiomerically pure sulfoxides.
Hydrogenative Kinetic Resolution of Vinyl Sulfoxides
Lao, Joan R.,Fernndez-Prez, Hctor,Vidal-Ferran, Anton
supporting information, p. 4114 - 4117 (2015/09/01)
Enantiopure sulfoxides are valuable precursors of organosulfur compounds with broad application in organic and pharmaceutical chemistry. An unprecedented strategy for obtaining highly enantioenriched sulfoxides based on a hydrogenative kinetic resolution using Rh-complexes of phosphine-phosphite ligands as catalysts is reported. After optimization, highly efficient conditions for the kinetic resolution of racemic sulfoxides have been identified. This methodology has been applied to a set of racemic aralkyl or aryl vinyl sulfoxides and allowed the isolation of both recovered and reduced products in excellent yields and enantioselectivities (up to 99% and 97% ee, respectively; 16 examples).
Sulfoxide-to-sulfilimine conversions: Use of modified Burgess-type reagents
Hendriks, Christine M. M.,Lamers, Philip,Engel, Julien,Bolm, Carsten
, p. 3363 - 3368 (2013/12/04)
Sulfoxides can directly be converted into N-cyanosulfilimines using a new Burgess-type reagent. By applying this strategy with a related reagent variant, synthetically valuable NH-sulfoximines have been prepared from sulfoxides via N-protected sulfilimines. The practical three-step reaction sequence is generally high yielding and applicable to a wide range of substrates. The sulfoxide-to-sulfilimine conversion can also be performed under solvent-reduced conditions in a ball mill. Copyright
Selective oxidation of sulfides to sulfoxides/sulfones by 30% hydrogen peroxide
He, Ying,Ma, Xiaoyun,Ji, Hai Feng,Zha, Xin Bing,Jiang, Hongliang,Lu, Ming
experimental part, p. 822 - 830 (2012/08/07)
A selective and efficient procedure for the oxidation of various sulfides with sodium tungstate dihydrate with 30% hydrogen peroxide in the presence of trioctylmethylammonium dihydrogen phosphate, respectively, to the corresponding sulfoxides and sulfones is reported. The oxidation reaction is carried out at -5 to 0 °C in the presence of hydroxypropyl -β cyclodextrins for sulfoxides or at 50-60 °C for sulfones. The mild reaction conditions, easy workup, and good yields of the products are the major advantages of this method. Copyright Taylor and Francis Group, LLC 2012.
Exploring the biocatalytic scope of a bacterial flavin-containing monooxygenase
Rioz-Martinez, Ana,Kopacz, Malgorzata,De Gonzalo, Gonzalo,Torres Pazmino, Daniel E.,Gotor, Vicente,Fraaije, Marco W.
experimental part, p. 1337 - 1341 (2011/04/23)
A bacterial flavin-containing monooxygenase (FMO), fused to phosphite dehydrogenase, has been used to explore its biocatalytic potential. The bifunctional biocatalyst could be expressed in high amounts in Escherichia coli and was able to oxidize indole and indole derivatives into a variety of indigo compounds. The monooxygenase also performs the sulfoxidation of a wide range of prochiral sulfides, showing moderate to good enantioselectivities in forming chiral sulfoxides. The Royal Society of Chemistry 2011.
Turning a riboflavin-binding protein into a self-sufficient monooxygenase by cofactor redesign
De Gonzalo, Gonzalo,Smit, Christian,Jin, Jianfeng,Minnaard, Adriaan J.,Fraaije, Marco W.
supporting information; experimental part, p. 11050 - 11052 (2011/12/01)
By cofactor redesign, self-sufficient monooxygenases could be prepared. Tight binding of N-alkylated flavins to riboflavin-binding protein results in the creation of artificial flavoenzymes capable of H2O 2-driven enantioselective sulfoxidations. By altering the flavin structure, opposite enantioselectivities could be achieved, in accordance with the binding mode predicted by in silico flavin-protein docking of the unnatural flavin cofactors. The study shows that cofactor redesign is a viable approach to create artificial flavoenzymes with unprecedented activities.
The X-ray structures of sulfoxides
Fuller, Amy L.,Aitken, R. Alan,Ryan, Bruce M.,Slawin, Alexandra M. Z.,Woollins, J. Derek
experimental part, p. 407 - 415 (2010/04/06)
We have structurally characterized and investigated a range of sulfoxide compounds containing aryl and alkyl substituents. Compounds 1 and 3-6 all crystallize in an orthorhombic space group, where compounds 2 and 7 crystallize in a monoclinic space group.
Photosensitized electron transfer oxidation of sulfides: A steady-state study
Bonesi, Sergio M.,Fagnoni, Maurizio,Albini, Angelo
scheme or table, p. 2612 - 2620 (2009/04/05)
The photosensitized electron-transfer oxidation of a series of ethyl sulfides RSEt (1, R = C12H25; 2, PhCH2CH 2; 3, PhCH2; 4, PhCMe2; 5, Ph2CH) has been examined in acetonitrile and the product distribution discussed on the basis of the mechanisms proposed. In nitrogen-flushed solutions, cleaved alcohols and alkenes are formed, whereas under oxygen, in reactions that are 10-70 times faster, sulfoxides and cleaved aldehydes and ketones are formed in addition to the afore-mentioned products. Two sensitizers are compared, 9,10-dicyanoanthracene (DCA) and 2,4,6-triphenylpyrylium tetrafluoroborate (TPP+BF4-), the former giving a higher proportion of the sulfoxide, the latter of cleaved carbonyls. The sulfoxidation is due to the contribution of the singlet oxygen path with DCA. Oxidative cleavage, on the other hand, occurs both with DCA and with TPP+ which is known to produce neither singlet oxygen nor the superoxide anion. This process involves deprotonation from the α position of the sulfide radical cation, but the TPP+ results suggest that O2.- is not necessarily involved and non-activated oxygen forms a weak adduct with the radical cation promoting α-hydrogen transfer, particularly with benzylic derivatives. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
