Month: October 2022

Ren, Jing; Jia, Meng-Cheng; Du, Feng-Huan; Zhang, Chi published the artcile< A general method for one-step synthesis of monofluoroiodane(III) reagents using silver difluoride>, Synthetic Route of 1391728-13-4, the main research area is iodobenzene silver difluoride oxidative fluorination; aryl monofluoroiodane preparation.

A new general method for one-step synthesis of four kinds of fluoroiodane(III) reagents by treating the corresponding aryl iodides with silver difluoride (AgF2) was reported. This is the first method applicable for the synthesis of all four fluoroiodane(III) reagents including p-iodotoluene difluoride, fluoro-benziodoxoles, fluoro-benziodoxolones and fluoro-N-acetylbenziodazole. AgF2 was firstly employed in the direct oxidative fluorination of iodobenzene and thus has shown its outstanding oxidation and fluorine-transfer ability. The use of AgF2 has improved the synthesis of fluoroiodane(III) reagents by shortening the reaction steps, avoiding the use of hazardous reagents and simplifying the exptl. operations. It was worth noting that the developed first one-step direct synthetic method for fluoro-benziodoxolones, while fluoro-benziodoxolones can only be synthesized through Cl→F ligand exchange reaction previously.

Chinese Chemical Letters published new progress about Benzoic acids Role: RCT (Reactant), RACT (Reactant or Reagent). 1391728-13-4 belongs to class iodides-buliding-blocks, and the molecular formula is C9H10FIO, Synthetic Route of 1391728-13-4.

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Polivkova, Jana; Piotrowski, David W. published the artcile< Stereodefined Cyclopentanes by Hydroarylation-Ring Opening>, Category: iodides-buliding-blocks, the main research area is stereodefined cyclopentane preparation; hydroarylation azabicycloheptenone nucleophilic ring opening.

The hydroarylation of 2-azabicyclo[2.2.1]hept-5-en-3-one followed by nucleophilic ring opening was employed as an operationally simple route to stereodefined trisubstituted cyclopentane analogs. This synthetic sequence was successfully executed using a variety of nucleophiles including hydroxide, alkoxide, hydride, Grignard reagents, and amines. E.g., hydroarylation of rac-2-azabicyclo[2.2.1]hept-5-en-3-one with PhI, followed by reaction with di-tert-Bu dicarbonate, gave 15% I and 25% II. Ring opening of II with LiOH in water gave 71% cyclopentane derivative (III). This methodol. facilitated the preparation of a constrained version of dipeptidylpeptidase 4 inhibitor sitagliptin.

Synthetic Communications published new progress about Diastereoselective synthesis. 2265-92-1 belongs to class iodides-buliding-blocks, and the molecular formula is C6H3F2I, Category: iodides-buliding-blocks.

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Liu, Yuliang; Li, Haoyu; Chiba, Shunsuke published the artcile< Photoinduced Cross-Coupling of Aryl Iodides with Alkenes>, HPLC of Formula: 887266-99-1, the main research area is aryl iodide alkene photoinduced cross coupling UV absorption.

A protocol for photoinduced cross-coupling of aryl iodides having polar π-functional groups or elongated π-conjugation with alkenes was developed. The radical cascade mechanism involving generation of aryl radicals via C-I bond homolysis of photoexcited aryl iodides and their subsequent addition to alkenes was proposed. The method enabled iodide-selective cross-coupling over other halogen leaving groups with functional group compatibility on both arene and alkene motifs.

Organic Letters published new progress about Aralkyl ketones Role: SPN (Synthetic Preparation), PREP (Preparation). 887266-99-1 belongs to class iodides-buliding-blocks, and the molecular formula is C7H3FIN, HPLC of Formula: 887266-99-1.

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Sugihara, Naoki; Suzuki, Kensuke; Nishimoto, Yoshihiro; Yasuda, Makoto published the artcile< Photoredox-Catalyzed C-F Bond Allylation of Perfluoroalkylarenes at the Benzylic Position>, Name: 3-Fluoro-4-iodobenzonitrile, the main research area is pperfluoroalkylarene allylic stannane defluoroallylation iridium photoredox catalyst.

Site-selective and direct C-F bond transformation of perfluoroalkylarenes was achieved with allylic stannanes via an iridium photoredox catalyst system. The present defluoroallylation proceeds exclusively at the benzylic position through perfluoroalkyl radicals generated by a single-electron transfer from an excited photoredox catalyst to perfluoroalkylarenes. A variety of perfluoroalkyl groups are applicable: linear perfluoroalkyl-substituted arenes such as Ar-nC4F9 and Ar-nC6F13 and heptafluoroisopropylarenes (Ar-CF(CF3)2) underwent site-selective defluoroallylation. DFT calculation studies revealed that the in situ generated Bu3SnF traps F- to prevent a retroreaction from the unstable perfluoroalkyl radical intermediate, and the radical intermediate favorably reacts with allylic stannanes. The synthesis of a bis(trifluoromethyl)methylene unit containing compound, which is an analog that is useful as a pharmaceutical agent for the prophylaxis or treatment of diabetes and inflammatory diseases, demonstrated the utility of this reaction.

Journal of the American Chemical Society published new progress about Allylation (defluoro-. 887266-99-1 belongs to class iodides-buliding-blocks, and the molecular formula is C7H3FIN, Name: 3-Fluoro-4-iodobenzonitrile.

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Granados, Albert; Ballesteros, Anna; Vallribera, Adelina published the artcile< Enantioenriched quaternary α-pentafluoroethyl derivatives of alkyl 1-indanone-2-carboxylates>, Name: 1-Fluoro-3,3-dimethyl-1,2-benziodoxole, the main research area is enantioenriched pentafluoroethylated alkyl indanone carboxylate preparation pybox ligand catalyst; pentafluoroethylation alkyl indanone carboxylate pybox ligand catalyst.

An electrophilic enantioselective catalytic method for the α-pentafluoroethylation of 3-oxoesters is described. Under the use of La(OTf)3 in combination with a (S,R)-indanyl-pybox ligand, good results in terms of yield and enantioselectivities were achieved (up to 89% ee). The reaction proceeds under mild conditions, leading to the formation of enantioenriched quaternary centers. This methodol. uses an hypervalent iodine(III)-CF2CF3 reagent, and mechanistic investigations are consistent with the involvement of a radical pathway. An electrophilic enantioselective catalytic method for the α-pentafluoroethylation of alkyl 1-indanone-2-carboxylates is described. Under the use of La(OTf)3 in combination with (S,R)-indanyl-pybox ligand good results in terms of yield and enantioselectivities were achieved (up to 89% ee). The reaction proceeds under mild conditions leading to the formation of enantioenriched quaternary centers. This methodol. uses an hypervalent iodine(III)-CF2CF3 reagent and mechanistic investigations are consistent with the involvement of a radical pathway.

Journal of Organic Chemistry published new progress about Absolute configuration. 1391728-13-4 belongs to class iodides-buliding-blocks, and the molecular formula is C9H10FIO, Name: 1-Fluoro-3,3-dimethyl-1,2-benziodoxole.

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Hughes, Gregory; Kreher, David; Wang, Changsheng; Batsanov, Andrei S.; Bryce, Martin R. published the artcile< Ethynyl π-extended 2,5-diphenyl-1,3,4-oxadiazoles and 2-phenyl 5-(2-thienyl)-1,3,4-oxadiazoles: synthesis, X-ray crystal structures and optical properties>, SDS of cas: 88105-22-0, the main research area is butylphenyl ethynylphenyl oxadiazole heteroaryl iodide Sonogashira cross coupling palladium; heteroarylethynylphenyl oxadiazole preparation optical property; ethynylthienyl oxadiazole heteroaryl iodide Sonogashira cross coupling palladium; oxadiazole phenyl ethynylthienyl preparation optical property crystal structure.

2-(4-Tert-Butylphenyl)-5-(4-ethynylphenyl)-1,3,4-oxadiazole (I, R = H) reacted with a series of heteroaryl iodides under standard Sonogashira cross-coupling conditions to yield products I [R = 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyrazyl (II), 5-bromo-2-pyrimidyl, 2-thienyl (III) and 3-thienyl (IV)] in 40-79% yields. Compound III was lithiated followed by electrophilic iodination using perfluorohexyl iodide to give the corresponding iodothienyl derivative, which by a two-step sequence gave the terminal ethynylthienyl derivative V (R’ = H) . Conversion of V into the terminal ethynylaldehyde derivative V (R’ = CHO) via acetal derivative proceeded in high yield. Starting from 2-iodo-5-methoxycarbonylthiophene, a five-step sequence afforded 2-(4-tert-butylphenyl)-5-(4-ethynylthienyl)-1,3,4-oxadiazole (VI, R = H) (13% overall yield). Sonogashira cross-coupling reactions of VI with heteroaryl iodides gave 2-phenyl-5-(2-thienyl)-1,3,4-oxadiazoles VI (R = 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyrazyl (VII), 5-bromo-2-pyrimidyl, 2-thienyl and 3-thienyl). Two-fold reaction of V with 2,5-diiodothiophene gave the bis(ethynylthienyl)thiophene derivative (30% yield). Solution UV-Vis absorption and photoluminescence spectra establish that replacement of the Ph ring in the 2,5-diphenyl-1,3,4-oxadiazole series I by a thienyl ring as in VI leads to a red shift in the lowest energy band in both the absorption spectra and emission spectra. The X-ray crystal structures of compounds II, IV, V and VII·CHCl3 reveal that the mol. structures are approx. planar although there are substantial differences in the conformations.

Organic & Biomolecular Chemistry published new progress about Aryl iodides Role: RCT (Reactant), RACT (Reactant or Reagent). 88105-22-0 belongs to class iodides-buliding-blocks, and the molecular formula is C6H5IO2S, SDS of cas: 88105-22-0.

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Matsumoto, Koki; Nakajima, Masaya; Nemoto, Tetsuhiro published the artcile< Determination of the best functional and basis sets for optimization of the structure of hypervalent iodines and calculation of their first and second bond dissociation enthalpies>, Recommanded Product: 1-Fluoro-3,3-dimethyl-1,2-benziodoxole, the main research area is hypervalent iodine bond dissociation enthalpy substituent effect.

Hypervalent iodines are widely used in organic chem., and their most important feature is the three-center four-electron bond. However, there have been few reports on the measurement of their bond dissociation enthalpy (BDE). Therefore, in many cases, BDE is estimated by computational calculations However, the value of a calculated BDE usually varies depending on the choice of functional and basis set, and the best method for making an accurate evaluation of the three-center four-electron bond has not been determined We succeeded in determining the best functional and basis set to calculate the three-center four-electron bond to within 0.79% error and 0.53 standard deviation. Using the optimal functional and basis set, the first and second BDEs of several hypervalent iodines are calculated, and as the effect of benzene substituents was investigated, neg. correlation was observed in the Hammett plot. In addition, the effect of ortho-substituent in cyclic hypervalent iodine was found to be significant. Furthermore, the decomposition route of hypervalent iodine is calculated The value of a calculated BDE usually varies depending on the choice of functional and basis set. We succeeded in determining the best functional and basis sets to calculate the three-center four-electron bond of hypervalent iodine to within 0.79% error and 0.53 standard deviation. Using the optimal functional and basis sets, the first and second BDEs of several hypervalent iodines are calculated, and addnl., the decomposition route of hypervalent iodine is calculated

Journal of Physical Organic Chemistry published new progress about Bond cleavage. 1391728-13-4 belongs to class iodides-buliding-blocks, and the molecular formula is C9H10FIO, Recommanded Product: 1-Fluoro-3,3-dimethyl-1,2-benziodoxole.

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Abraham, Raymond J.; Cooper, M. Ashley published the artcile< A re-investigation of 4JFF and 5JFF nuclear spin-spin couplings in substituted benzenes, a novel conformational tool>, COA of Formula: C6H3F2I, the main research area is benzene nuclear spin coupling B3LYP.

A theor. anal. of the 4JFF and 5JFF couplings in fluorobenzenes separates the σ and π components of the substituent coefficients The π bond mechanism is dominant but the σ bond mechanism must be included to give accurate values of the couplings. For monosubstituted difluorobenzenes the 4JFF and 5JFF couplings can be predicted from the calculated π densities by linear equations. The use of additive substituent effects allows the prediction of the meta4JFF couplings for multisubstituted compounds The π dependence of the 4JFF coupling in 2,6-difluorobenzenes provides a novel and simple method of determining the torsional angle of the C1 substituent and the benzene ring for non-sym. functional groups (acetyl, carboxymethyl, dimethylamino, amide, nitro etc.). This could be used to determine the geometries of such mols. in biol. systems. The π dependence of the 4JFF coupling is also of importance in the charged species of 2,6-difluoroanilinium (4JFF 2.1 Hz) and 2,6-difluoro-N,N,N-trimethylanilinium (4JFF 0.0 Hz) due to the very different π electron densities.

Physical Chemistry Chemical Physics published new progress about Bond angle, torsional. 2265-92-1 belongs to class iodides-buliding-blocks, and the molecular formula is C6H3F2I, COA of Formula: C6H3F2I.

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com