TCI Chemistry News
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November 2022
TCI offers an extensive catalog of 31,000 high quality organic reagents suitable for benchtop-to-bulk chemistry. This issue covers our chemistry topics as follows.
- C(sp2)-C(sp3) Cross-Coupling Reactions for Drug Discovery
- Organocatalyst for Electrophilic Halogenation of Aromatic Compounds under Mild Conditions
- The Synthesis of the C-Aryl Glycoside through the Cross-Coupling of the Glycosyl Dihydoropyridinecarboxylic Acid Precursor
- Regioselective Iodination Using Iodine and Silver Nitrate
C(sp2)-C(sp3) Cross-Coupling Reactions for Drug Discovery
β-Hydrogen elimination and transmetalation from aliphatic compounds are regarded as bottlenecks, in the field of C-C bond formation between aromatic and aliphatic compounds. Recently, a variety of C(sp2)-C(sp3) cross-coupling reactions utilizing the combination of visible light photoredox catalysts and transition metal catalysts like nickel catalysts have been reported. Moreover, reductive cross-electrophile coupling between aryl halides and alkyl halides enabled reproductive introduction of alkyl groups into (hetero)aromatic compounds. Alkyl halides, alkylcarboxylic acids, and alkyl amines can be applied as coupling partners in these reactions. They are easier to find commercially than organozincs, organoboronic acids and Grignard reagents. We show examples of representative C(sp2)-C(sp3) cross-coupling reactions using them as coupling partners.
Organocatalyst for Electrophilic Halogenation of Aromatic Compounds under Mild Conditions
Halogen groups are one of the most important functional groups in synthetic chemistry. They act as a starting point for functional group transformations. On the other hand, a halogenation reaction with high selectivity and reactivity still remains a challenge. Trip-SMe [D6031], an organocatalyst for the electrophilic halogenation of aromatic C-H bond has been reported. In the presence of Trip-SMe and a cocatalyst, halogenation of aromatic compounds with N-halosuccinimides proceeds regioselectively under mild conditions.
TCI Practical Example: The Synthesis of the C-Aryl Glycoside through the Cross-Coupling of the Glycosyl Dihydoropyridinecarboxylic Acid Precursor
TCI introduces the synthesis of the C-aryl glycoside catalyzed by a photoredox catalyst. The glycosyl ester is prepared by condensation of 3,5-bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine-4-carboxylic acid [B6316] and 2,3,5-tri-O-benzyl-α/β-D-ribofuranose, and is utilized as radical precursors. C-aryl glycoside is synthesized via the cross-coupling reaction of a glycosyl radical which is generated from the precursor by a photoredox catalyst.
TCI Practical Example: Regioselective Iodination Using Iodine and Silver Nitrate
We are pleased to introduce the use of silver nitrate and iodine [I0604] for the ortho-selective iodination of 3-benzyloxyphenylboronic acid. Iodinating agents are shown in the TCI product brochure.Upcoming Events
Asia-Pacific International Conference on Perovskite, Organic Photovoltaics and Optoelectronics (IPEROP23)
January 22-24, 2023
Kobe Convention Center, Japan
January 22-24, 2023
Kobe Convention Center, Japan
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