TCI Chemistry News
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April 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:
- N-Hydroxyphthalimide Derivatives for the Synthesis of Redox Active Esters
- Easy-to-Handle Electrophilic Vinylating Reagent
- Pyrylium Salt for Nucleophilic Aromatic Substitution Reactions of Amino Heteroaromatics
- Iridium Catalyst for Hydrogenolysis of Urea Derivatives to Formamides and Amines under Mild Conditions
- TCIMAIL 195

N-Hydroxyphthalimide Derivatives for the Synthesis of Redox Active Esters
4-Methyl-N-hydroxyphthalimide [M3571] and 4-methoxy-N-hydroxyphthalimide [M3572] condense with aliphatic carboxylic acids to produce electron-rich redox active esters (RAEs). It has been reported that the reduction potential is lower than that of conventional RAEs and suppression of side reactions. The resulting RAE can be used for C(sp3)-C(sp3) cross-coupling reactions with inert alkyl bromides.

Easy-to-Handle Electrophilic Vinylating Reagent
5-Vinyl-5H-thianthren-5-ium tetrafluoroborate [E1521] is an electrophilic vinylating reagent whose structure is a thianthrenium salt substituted by ethylene. This is a non-hygroscopic solid, so it is easier to handle compared to gas when used for vinylation such as vinyl bromide, and can be used in a variety of electrophilic vinylation reactions.

Pyrylium Salt for Nucleophilic Aromatic Substitution Reactions of Amino Heteroaromatics
Pyrylium tetrafluoroborate [P2823] activates the amino group of amino heteroaromatics, and converts to the leaving group. The resulting pyridinium salts can be applied to aromatic nucleophilic substitution reactions under mild conditions without purification. This reagent is suitable for late-stage functionalization due to the high functional-group tolerance.

Iridium Catalyst for Hydrogenolysis of Urea Derivatives to Formamides and Amines under Mild Conditions
Iridium catalyst [C4021] catalyzes the decomposition of urea derivatives to formamides and amines. It can be used under mild conditions and its application of gram-scale or with very low amount of catalyst usage have been reported. It is applicable to asymmetric urea derivatives and polyureas.

Printed Magazine: TCIMAIL 195
Released in March 2024, TCI's latest issue features Prof. Hiroshi Shinokubo and coworkers’ article “Development of typical-element-doped functional π-systems consisting of naphthalene monoimide units” and Teacher Hiroyuki Onuki's chemistry chat “Difficulties in Senior High School Chemistry Experiments”.
We also feature research on:
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