The reaction between acyl halides and alcohols: Alkyl halide vs. Ester formation

Formamides as Lewis Base Catalysts in SN Reactions—Efficient Transformation of Alcohols into Chlorides, Amines, and Ethers

“…We envisioned that the less‐acidic conditions could result in improved functional group compatibility and selectivity. While the reaction of alcohols with carboxylic acid chlorides usually provides the corresponding esters, we herein present a first and highly efficient method for the chlorination of alcohols employing inexpensive benzoyl chloride (BzCl, 4 a ) as the exclusive reagent in the presence of a simple formamide as catalyst…”

“…We envisioned that the less-acidic conditions could result in improved functional group compatibility and selectivity. While the reaction of alcohols with carboxylic acid chlorides usually provides the corresponding esters, [11] we herein present afirst and highly efficient method for the chlorination of alcohols employing inexpensive benzoyl chloride (BzCl, 4a)a st he exclusive reagent in the presence of as imple formamide as catalyst. [12,13] In an initial screening utilizing benzylic alcohol 1 1 and various carboxylic acid chlorides in the presence of 10 mol % of DMF,BzCl was identified as the optimum reagent (Table 1, entry 1; see also Schemes S5,S6, in the Supporting Information).…”

Formamide als Lewis‐Basen‐Katalysatoren in SN‐Reaktionen: Effiziente Transformationen von Alkoholen zu Chloriden, Aminen und Ethern

“…B. Benzoesäure 6 a ) als einziges und nur schwach saures Nebenprodukt entstehen: Die milderen Reaktionsbedingungen versprechen eine verbesserte Selektivität und Kompatibilität mit funktionellen Gruppen. Während die Reaktion von Alkoholen mit Carbonsäurechloriden normalerweise die entsprechenden Ester liefert, stellen wir eine erste und hocheffiziente Methode zur Chlorierung von Alkoholen mit preiswertem Benzoylchlorid (BzCl, 4 a ) als exklusivem Reagenz in der Gegenwart von einfachen Formamiden als Katalysatoren vor…”

Polymer-supported N-heterocyclic carbene–rhodium complex catalyst for the addition of arylboronic acids to aldehydes

“…1 Other addition products, diphenylmethanol [11,39], 4-chlorodiphenylmethanol [39], 4-nitrodiphenylmethanol [40], 4-cyanodiphenylmethanol [11,41], 1,3-benzodioxol-5-ylphenylmethanol [42], 4-chloro-4 0 -methyldiphenylmethanol [41], 4-methyl-4 0 -nitrodiphenylmethanol [43], 4-cyano-4 0 -methyldiphenylmethanol [41], 4-chloro-4 0 -methoxyldiphenylmethanol [44,45] have been identified by comparing their 1 H NMR spectra and melting points with that reported in the literature.…”