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.

• Mono-functionalized β-Cyclodextrins
• Agent for the C-H Nitration and the Construction of Isoxazoline Ring
• Conversion of Carbonyl Group into Thiocarbonyl Group using Lawesson's Reagent
• Protection of the Boronic Acid with 1,8-Diaminonaphthalene
• Suzuki-Miyaura Coupling of Diaminonaphthalene (dan)-Protected Bromophenylboronic Acid

Mono-functionalized β-Cyclodextrins

Cyclodextrin scaffolds have been applied not only in the field of functional materials such as self-repairing polymers, but also DDS as siRNA carrier. TCI offers an extensive line-up of mono-functionalized cyclodextrins based on the regioselective functionalization technology of β-cyclodextrins. In particular mono-6- O -(p-toluenesulfonyl)-β-cyclodextrin [M3398] , one of the typical building blocks, has achieved high purity of at least 95% by HPLC by significantly reducing the content of multisubstituted byproducts. In addition, cyclodextrin structures can be introduced into target molecules by using click reactions utilizing the azide group of 6A-azido-6A-deoxy-β-cyclodextrin [A3454] and condensation reactions utilizing the amino group of 6A-amino-6A-deoxy-β-cyclodextrin [A3453] .

Agent for the C-H Nitration and the Construction of Isoxazoline Ring

N -Nitrosuccinimide [N1193] is a stable solid and can be utilized in photoredox nitration reactions. When styrene is treated with N1193 and Ru(bpy) ₃ (PF ₆ ) ₂ as a photocatalyst under the irradiation of LED light, the alkene moiety is selectively nitrated at terminal position. Furthermore, the palladium-free ipso -nitration of arylboronic acids proceeds under the photoredox condition. As another example, the construction of isoxazoline ring can be raised through the multi-component reaction of N1193, alkene, or alkyne in acetone solvent.

TCI Practical Example: Conversion of Carbonyl Group into Thiocarbonyl Group using Lawesson's Reagent

We are proud to present the reaction which converts the carbonyl group of 2-pyrrolidone to a thiocarbonyl group using Lawesson's Reagent [B1133] . The reaction was carried out in a fume hood due to the bad smell of Lawesson’s reagent.

TCI Practical Example: Protection of the Boronic Acid with 1,8-Diaminonaphthalene

TCI introduces the protection of 3,5-dibromophenylboronic acid with 1,8-diaminonaphthalene [D0102] . The reaction report is actually performed by TCI's synthesis staff. You can see not only the reaction procedure but also the comments and analysis data from our staff.

TCI Practical Example: Suzuki-Miyaura Coupling of Diaminonaphthalene (dan)-Protected Bromophenylboronic Acid

2-(4-Bromophenyl)-2,3-dihydro-1 H -naphtho[1,8- de ][1,3,2]diazaborine [B3655] can be synthesized from 4-bromophenylboronic acid and 1,8-diaminonaphthalene (dan) by the protection reaction introduced in the previous section. This section shows the Suzuki-Miyaura coupling of the stable B3655 with 4-(ethoxycarbonyl)phenylboronic acid . The dan group can be deprotected by acidic condition and the free boronic acid can be easily obtained. » TCI eNewsletter Back Issues

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