76358-92-4

Upstream product

• 586-98-1 2-Hydroxymethylpyridine 
• 71098-88-9 N-phenylselanylphthalimide 
• 5707-04-0 Phenylselenyl chloride 
• 109-06-8 α-picoline 
• 1666-13-3 diphenyl diselenide 
• 106966-98-7 potassium 2-(pyridin-2-yl)acetate 
• 591-50-4 iodobenzene 
• 43071-19-8 2-[(Dimethylamino)methyl]pyridine 
• 4377-33-7 2-chloromethylpyridine 
• 31106-82-8 2-(bromomethyl)pyridine hydrobromide 
• 2179-79-5 phenyl selenocyanate 

Downstream Products

• 4916-40-9 1,2-bis(pyridin-2-yl)ethane 
• 1666-13-3 diphenyl diselenide 
• 404361-95-1 Pd(0)(η2-fumaronitrile)(C5H4NCH2SeC6H5) 
• 1206594-85-5 PdCl₂(2-phenylselenomethylpyridine) 
• 1268397-94-9 N-methyl 2-(phenylselenomethyl)pyridinium triflate 
• 1370620-98-6 ((C₅(CH₃)5)IrCl(NC₅H₄CH₂SeC₆H₅))⁽¹⁺⁾*PF₆^(1-)=((C₅(CH₃)5)IrCl(NC₅H₄CH₂SeC₆H₅))PF₆ 
• 1441253-24-2 [ruthenium(II)(η⁶-benzene)(chloride)(NC5H4CH2SeC6H5)](hexafluorophosphate) 
• 78808-34-1 9-anthrylmethyl phenyl selenide 
• 18255-05-5 benzyl phenyl selenide 

Relevant academic research and scientific papers

Metal-free synthesis of unsymmetrical selenides from pyridinium salts and diselenides catalysed by visible light

We report the first metal-free selenolations of pyridinium salts with diselenides to prepare unsymmetrical organoselenides catalysed by visible light. This protocol is an efficient and green method for the preparation of unsymmetrical organoselenides because metal-free conditions and readily accessible diselenides are used.

Transition-metal-free decarboxylative thiolation of stable aliphatic carboxylates

A transition-metal-free decarboxylative thiolation protocol is reported in which primary, secondary, tertiary (hetero)aryl acetates and α-CN substituted acetates undergo the decarboxylative thiolation smoothly, to deliver a variety of functionalized aryl alkyl sulfides in moderate to excellent yields. Aryl diselenides are also amenable substrates for construction of C-Se bonds under the simple and mild reaction conditions. Moreover, the protocol is successfully applied to the late-stage modification of pharmaceutical carboxylates with satisfactory chemoselectivity and functional-group compatibility. This journal is

Transition metal-free coupling reactions of benzylic trimethylammonium salts with di(hetero)aryl disulfides and diselenides

A new protocol was developed to synthesize (enantioenriched) thioethers and selenoethers from (chiral) benzylic trimethylammonium salts and di(hetero)aryl disulfides or diselenides. These syntheses were promoted by the presence of weak base and did not require the use of any transition metal, and resulted in the target products with good to excellent yields (72-94%). Using quaternary ammonium salts synthesized from enantiomerically enriched amines led to highly enantiopure benzylic thioethers and selenoethers (94-99% ee) with configurations reversed from those of their enantioenriched quaternary ammonium salts. This journal is

Regioselective Synthesis of 1-Sulfanyl- and 1-Selanylindolizines

We describe herein a new approach to prepare unprecedented bioactive indolizine motifs decorated with organosulfur and organoselenium groups. A total of 12 1-sulfanylindolizines and 2 1-selanylindolizines were prepared in excellent yields by an intramolecular annulation of easily prepared chalcogen-containing pyridinium salts. The reaction is fast (1 h at 70 °C or 5 min under sonication) and transition-metal-free, using glycerol as a green solvent.

Metal-free sp3 C-H functionalization: A novel approach for the syntheses of selenide ethers and thioesters from methyl arenes

A DTBP-promoted metal-free and solvent-free formation of C-Se and C-S bonds through sp3 C-H functionalization of methyl arenes with diselenides and disulfides is described. the Partner Organisations 2014.

Orbital interactions in selenomethyl-substituted pyridinium ions and carbenium ions with higher electron demand

Computational, solution phase, and crystal structure analysis of 2- and 4-organoselenylmethyl-substituted pyridinium ions (10a-c and 11a-c) provides strong evidence for C-Se hyperconjugation (σC-Se-π*) between the C-Se σ-bond and the π-deficien

Synthesis and structure of dichloropalladium(II) complexes of heteroleptic N,S- and N,Se-donor ligands based on the 2-organochalcogenomethylpyridine motif, and Mizoroki-Heck catalysis mediated by complexes of N,S-donor ligands

Ligands containing the 2-organochalcogenomethylpyridine motif with substituents in the 4- or 6-position of the pyridyl ring, R4,R6-pyCH2ER1 [R4 = R6 = H, ER1 = SMe (1), SeMe (2), SPh (6), SePh (7); R4 = Me, R6 = H, ER1 = SMe (3), SPh (8), SePh (9); R4 = H, R6 = Me, ER1 = SMe (4), SPh (10), SePh (11); R4 = H, R6 = Ph, ER1 = SMe (5), SPh (12), SePh (13)] are obtained on the reaction of R4,R6-pyMe with LiBun followed by R1EER1. On reaction with PdCl2(NCMe)2, the ligands with a 6-phenyl substituent form cyclopalladated species PdCl{6-(o-C6H4)pyCH2ER1-C,N,E} (5a, 12a, 13a) with the structure of 13a (ER1 = SePh) confirmed by X-ray crystallography; other ligands form complexes of stoichiometry PdCl2(R4,R6-pyCH2ER1). Complexes with R6 = H are monomeric with N,E-bidentate configurations, confirmed by structural analysis for 3a (R4 = Me, ER1 = SMe), 7a (R4 = H, ER1 = SePh) and 9a (R4 = Me, ER1 = SePh). Two of the 6-methyl substituted complexes examined by X-ray crystallography are oligomeric with trans-PdCl2(N,E) motifs and bridging ligands, trimeric [PdCl2(μ-6-MepyCH2SPh-N,S)]3 (10a) and dimeric [PdCl2(μ-6-MepyCH2SePh-N,Se)]2 (11a). This behaviour is attributed to avoidance of the Me···Cl interaction that would occur in the cis-bidentate configuration if the pyridyl plane had the same orientation with respect to the coordination plane as observed for 3a, 7a and 9a [dihedral angles 8.0(2)-16.8(2)°]. When examined as precatalysts for the Mizoroki-Heck reaction of n-butyl acrylate with aryl halides in N,N-dimethylacetamide at 120 °C, the complexes exhibit the anticipated trends in yield (ArI > ArBr > ArCl, higher yield for electron withdrawing substituents in 4-RC6H4Br and 4-RC6H4Cl). The most active precatalysts are PdCl2(R4-pyCH2SMe-N,S) (R = H (1a), Me (3a)); complexes of the selenium containing ligands exhibit very low activity. For closely related ligands, the changes SMe to SPh, 6-H to 6-Me, and 6-H to 6-Ph lead to lower activity, consistent with involvement of both the pyridyl and chalcogen donors in reactions involving aryl bromides. The precatalyst PdCl2(pyCH2SMe-N,S) (1a) exhibits higher activity for the reaction of aryl chlorides in Bun4NCl at 120 °C as a solvent under non-aqueous ionic liquid (NAIL) conditions. Crown Copyright

N-PHENYLSELENOPHTHALIMIDE (NPSP) A VALUABLE SELENENYLATING AGENT

The phenylseleno group (PhSe) has evolved in recent years as a very useful and versatile functionality.Its facile introduction into organic molecules and its subsequent oxidative or reductive removal, has allowed many important synthetic transformations.D

Flash Pyrolysis of Selenides. Syntheses of Bibenzyls, Olefins, and Related Compounds

Pyrolyses of a series of selenides and diselenides were studied. Selenides and diselenides bound with an active methylene group like benzyl gave a variety of substituted bibenzyls and related ethane derivatives in high yields. Other diselenides were easily caused to cleave to give various aromatic and aliphatic olefins in good yields together with elemental selenium. Lepidopterene, paracyclophane, and benzocyclobutene were prepared by thermal cleavage of their corresponding phenylselenomethyl-substituted compounds as an application of the pyrolysis concerned.