866-72-8Relevant articles and documents
Hypervalent Iodine(III)-Mediated Decarboxylative Ritter-Type Amination Leading to the Production of α-Tertiary Amine Derivatives
Kiyokawa, Kensuke,Watanabe, Tomoki,Fra, Laura,Kojima, Takumi,Minakata, Satoshi
, p. 11711 - 11720 (2017/11/27)
α-Tertiary amines (ATAs) are attractive structural motifs that are frequently found in biologically active molecules. Therefore, the development of an efficient method for the synthesis of ATAs represents an important research topic in the field of medicinal chemistry as well as organic chemistry. Although the Ritter reaction is a reliable approach for preparing α-tertiary amine derivatives via intermolecular amination reactions, the typical methods suffer from disadvantages such as harsh reaction conditions and the use of strong acids. Because of this, it has been of limited use in the synthesis of ATAs. We report here on the decarboxylative Ritter-type amination of carboxylic acids bearing an α-quaternary carbon center using a combination of PhI(OAc)2 and molecular iodine (I2) to produce the corresponding α-tertiary amine derivatives. This reaction proceeded at ambient temperature on the benchtop with a fluorescent light. Mechanistic investigations suggest that the reaction proceeds via the formation of an alkyl iodide and a higher oxidation state iodine(III) species as key intermediates. Similarly, a stepwise protocol for the Ritter-type amination of alcohols via the formation of oxalic acid monoalkyl esters was also achieved. The present methods represent a useful tool for the synthesis of ATAs that are difficult to prepare by conventional methods.
HIGHLY SELECTIVE SYNTHESIS OF ACYCLIC TERT-ALIPHATIC CARBOXYLIC ACIDS FROM ACYCLIC TERT-ALCOHOLS USING SULFURIC ACID SUPERSATURATED WITH CARBON MONOXIDE
Takahashi, Yukio,Yoneda, Norihiko
, p. 1945 - 1954 (2007/10/02)
The selective carboxylation of acyclic tert-aliphatic alcohols was successfully performed to produce the corresponding acyclic tert-aliphatic carboxylic acids in significantly high yields using concentrated sufuric acid supersaturated with carbon monoxide.