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TCI Chemistry News  March 2021



TCI offers an extensive catalog of 30,000 high quality organic reagents suitable for benchtop-to-bulk chemistry. This issue covers the following topics:
-   a phthalimide derivative for selective iodination of acrylic esters,
-   pentafluoroethylation using economical ethyl pentafluoropropionate,
-   an iron complex catalyst for C-H borylation,
-   benzylation reagents.
Phthalimide Derivative for Selective Iodination of Acrylic Esters

A Phthalimide Derivative for Selective Iodination of Acrylic Esters

N-iodophthalimide [I1052] is utilized in the selective iodination at the α-position of acrylic esters. When acrylic esters react with I1052 in the presence of a catalytic amount of 3-quinuclidinol and KF-Celite under light-shielded conditions, the iodination proceeds via a Morita-Baylis-Hillman type reaction to give α-iodoacrylic esters in good yields. This reaction proceeds only with acrylic esters and not with α,β-unsaturated esters bearing a substituent at the β-position. Given products can be applied in cross couplings such as the Nozaki-Hiyama-Kishi reaction.
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Pentafluoroethylation Using Economical Ethyl Pentafluoropropionate

Pentafluoroethylation Using Economical Ethyl Pentafluoropropionate

Ethyl pentafluoropropionate [P1123] is used as a source of pentafluoroethyl moiety. When P1123 is added to a mixture of copper(I) chloride and potassium tert-butoxide, the pentafluoroethyl cuprate intermediate is formed in situ. Upon addition of boronic acids or aryl bromides in air or under argon atmosphere, respectively, the cross coupling proceeds and the pentafluoroethyl moiety is introduced. One of the advantages of this reaction is that it is economical to insert the pentafluoroethyl moiety because of the use of inexpensive reagents.
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Iron Complex Catalyst for C-H Borylation

An Iron Complex Catalyst for C-H Borylation

Dichloro[8-(diisopropylphosphino)-5-fluoro-2-(2-pyridinyl)quinoline]iron(II) [D5886], an iron complex bearing a quinoline-based PNN pincer ligand catalyzes the C-H borylation of (hetero)arenes. For example, it has been reported that the reaction with bis(pinacolato)diboron in the presence of D5886 and a base proceeds to give borylated toluenes, furans or thiophenes.
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Benzylation Reagents

Benzylation Reagents

Benzyl 2,2,2-trichloroacetimidate [B1483] is a benzylation reagent activated by acid-catalysts such as TfOH and used for the benzylation of base-sensitive substrates. Benzyl 2,2,2-trifluoro-N-phenylacetimidate [B3234] is more stable than B1483, and reacts even with hindered alcohols in the presence of a catalytic amount of TMSOTf in dioxane to produce the benzylated products in high yields.
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