TCI Chemistry News
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January 2024
TCI offers an extensive catalog of over 30,000 high quality organic reagents suitable for benchtop-to-bulk chemistry. This issue covers our chemistry topics as follows:
- Di(2-pycolyl)amine Ligands for Reductive Cross-Electrophile Coupling Reaction
- TCO (trans-cyclooctene) Reagents for Bioconjugate Reactions
- Suzuki-Miyaura Coupling Using Ni(COD)2
- Hosomi-Sakurai Allylation via an Imine Intermediate
Di(2-pycolyl)amine Ligands for Reductive Cross-Electrophile Coupling Reaction
In discovery research on small molecule drugs, C(sp2)-C(sp3) cross coupling reactions are very powerful methods. Especially, the cross coupling reactions between aryl halides and alkyl halides are known as reductive cross-electrophile coupling reactions (CEC, XEC), that attract a lot of attention due to the availability and stability of alkyl halides.We offer three DPA ligands, methylbis(2-pyridylmethyl)amine [M3627], 1-(4-methoxy-3,5-dimethylpyridin-2-yl)-N-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-N-methylmethanamine [M3633], N,N-Bis[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]cyclopropanamine [B6525]. When DPA ligands are used as catalysts for reductive cross-electrophile coupling reactions, it is reported that better results can be obtained than the standard ligand, dtbbpy. It is known that secondary alkyl bromides such as heterocyclic alkyl bromides and etc. than primary alkyl bromides. DPA ligands have been found to improve the product yields from some substrates. In addition, our products are useful for late-stage functionalization, parallel library synthesis and high-throughput experiments in the drug discovery research.
TCO (trans-cyclooctene) Reagents for Bioconjugate Reactions
TCO (trans-cyclooctene) is known as a compound that undergoes a Strain-Promoted Inverse Electron-demand Diels-Alder Cycloaddition (SPIEDAC) with tetrazines. This reaction is widely used in protein labeling and imaging as a bioconjugation reaction. 4-TCO-NPC equatorial isomer [T4212], 4-TCO-NPC axial isomer [T4213], 2-TCO-NPC axial isomer [T4218], and 2-TCO-NPC equatorial isomer [T4219] are regio- and stereoisomers of each other and have distinct reactivity. These reagents easily react with primary amines at the carbonate ester group to give the corresponding carbamates.
TCI Practical Example: Suzuki-Miyaura Coupling Using Ni(COD)2
TCI introduces the Suzuki-Miyaura cross coupling reaction of 4'-chloroacetophenone with phenylboronic acid using Ni(COD)2 [B6553]. B6553 may be partially discolored since it is unstable in the air, but it has been confirmed that there is no problem in its functionality through this experiment.
TCI Practical Example: Hosomi-Sakurai Allylation via an Imine Intermediate
We are proud to present the three component reaction of cyclopentanone, benzyl carbamate and allyl(trimethyl)silane [A0729] via the Hosomi-Sakurai allylation.Upcoming Events
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