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The oxidation of pyridine can be achieved with a number of peracids including peracetic acid and perbenzoic acid. [3] Oxidation can also be effected by a modified Dakin reaction using a urea-hydrogen peroxide complex, [4] and sodium perborate [5] or, using methylrhenium trioxide (CH 3 ReO 3) as catalyst, with sodium percarbonate. [6]
Protodeboronation is a well-known undesired side reaction, and frequently associated with metal-catalysed coupling reactions that utilise boronic acids (see Suzuki reaction). [1] For a given boronic acid, the propensity to undergo protodeboronation is highly variable and dependent on various factors, such as the reaction conditions employed and ...
Nicotinonitrile or 3-cyanopyridine is an organic compound with the formula NCC 5 H 4 N. The molecule consists of a pyridine ring with a nitrile group attached to the 3-position. A colorless solid, it is produced by ammoxidation of 3-methylpyridine: [2] H 3 CC 5 H 4 N + NH 3 + 1.5 O 2 → NCC 5 H 4 N + 3 H 2 O. Nicotinonitrile is a precursor to ...
Compounds of the type BR n (OR) 3-n are called borinic esters (n = 2), boronic esters (n = 1), and borates (n = 0). Boronic acids are key to the Suzuki reaction. Trimethyl borate, debatably not an organoboron compound, is an intermediate in sodium borohydride production.
The boron atom of a boronic ester or acid is sp 2 hybridized possessing a vacant p orbital, enabling these groups to act as Lewis acids. The C–B bond of boronic acids and esters are slightly longer than typical C–C single bonds with a range of 1.55-1.59 Å.
In the Chan–Lam coupling the alkyl, alkenyl or aryl boronic acid reacts with a N–H or O–H containing compound with Cu(II) such as copper(II) acetate and oxygen and a base such as pyridine [19] [20] forming a new carbon–nitrogen bond or carbon–oxygen bond for example in this reaction of 2-pyridone with trans-1-hexenylboronic acid:
Chlorpyrifos is produced from 3,5,6-trichloro-2-pyridinol, which is generated from 3-picoline by way of cyanopyridine. This conversion involves the ammoxidation of 3-methylpyridine: CH 3 C 5 H 4 N + 1.5 O 2 + NH 3 → NCC 5 H 4 N + 3 H 2 O. 3-Cyanopyridine is also a precursor to 3-pyridinecarboxamide, [3] [4] [5] which is a precursor to ...
The Suzuki reaction or Suzuki coupling is an organic reaction that uses a palladium complex catalyst to cross-couple a boronic acid to an organohalide. [1] [2] [3] It was first published in 1979 by Akira Suzuki, and he shared the 2010 Nobel Prize in Chemistry with Richard F. Heck and Ei-ichi Negishi for their contribution to the discovery and development of noble metal catalysis in organic ...