105336-31-0Relevant articles and documents
Visible-Light-Enabled Direct Decarboxylative N-Alkylation
Arman, Hadi D.,Dang, Hang T.,Haug, Graham C.,Larionov, Oleg V.,Nguyen, Viet D.,Nguyen, Vu T.,Vuong, Ngan T. H.
supporting information, p. 7921 - 7927 (2020/04/10)
The development of efficient and selective C?N bond-forming reactions from abundant feedstock chemicals remains a central theme in organic chemistry owing to the key roles of amines in synthesis, drug discovery, and materials science. Herein, we present a dual catalytic system for the N-alkylation of diverse aromatic carbocyclic and heterocyclic amines directly with carboxylic acids, by-passing their preactivation as redox-active esters. The reaction, which is enabled by visible-light-driven, acridine-catalyzed decarboxylation, provides access to N-alkylated secondary and tertiary anilines and N-heterocycles. Additional examples, including double alkylation, the installation of metabolically robust deuterated methyl groups, and tandem ring formation, further demonstrate the potential of the direct decarboxylative alkylation (DDA) reaction.
Reaction of 4-Bromo-1,2-dimethylbenzene with Various Nucleophiles via Aryne Reaction
Biehl, Edward R.,Razzuk, Aziz,Jovanovic, Misa V.,Khanapure, Subhash P.
, p. 5157 - 5160 (2007/10/02)
4-Bromo-1,2-dimethylbenzene (4a) reacts with a variety of amines, mercaptans, and nitriles under aryne-forming conditions to yield predominantly 4-substituted 1,2-dimethylbenzenes and minor quantities of 3-substituted 1,2-dimethylbenzenes.The product distributions from these reactions are heavily in favor of the 4-substituted isomer since it is formed exclusively from the symmetric 4,5-dimethylbenzyne intermediate (6) and partly from the unsymmetric 3,4-dimethylbenzyne intermediate (5).
