40577-05-7Relevant academic research and scientific papers
Ligand-free Iron(II)-Catalyzed N-Alkylation of Hindered Secondary Arylamines with Non-activated Secondary and Primary Alcohols via a Carbocationic Pathway
Nayal, Onkar S.,Thakur, Maheshwar S.,Kumar, Manoranjan,Kumar, Neeraj,Maurya, Sushil K.
supporting information, p. 730 - 737 (2017/12/26)
Secondary benzylic alcohols represent a challenging class of substrates for N-alkylation of amines. Herein, we describe an iron(II)-catalyzed eco-friendly protocol for N-alkylation of secondary arylamines with secondary benzyl alcohols through a carbocationic pathway instead of the known borrowing hydrogen transfer (BHT) approach. Transiently generated carbocations, produced from alcohols via self-condensation, were coupled with arylamines to provide highly functionalized amine products. The scope of this methodology involves N-alkylation of primary, secondary and heterocyclic amines with primary/secondary benzylic, allylic and heterocyclic alcohols, which are common key structures in numerous pharmaceuticals drugs. The method can also be easily adopted for the amination of various natural products. (Figure presented.).
Synthesis of tertiary arylamines: Lewis acid-catalyzed direct reductive: N -alkylation of secondary amines with ketones through an alternative pathway
Nayal, Onkar S.,Thakur, Maheshwar S.,Bhatt, Vinod,Kumar, Manoranjan,Kumar, Neeraj,Singh, Bikram,Sharma, Upendra
supporting information, p. 9648 - 9651 (2016/08/04)
We report herein a highly efficient, tin(ii)/PMHS catalyzed reductive N-alkylation of arylamines with ketones affording tertiary arylamines. A very wide substrate scope was observed for the current catalytic method as all six permutations of ketones/aldehydes/heterocyclic carbonyls and primary/secondary/heterocyclic amines were well tolerated, enabling access to secondary, tertiary and heterocyclic amines. The method is also convenient for the synthesis of N-substituted isoindolinones and phthalazinones via a tandem amination-amidation sequence. Mechanistic investigations revealed a carbocationic pathway instead of an ordinary direct reductive amination pathway.
