70623-01-7Relevant articles and documents
Tropylium-promoted Ritter reactions
Doan, Son H.,Hussein, Mohanad A.,Nguyen, Thanh Vinh
supporting information, p. 8901 - 8904 (2021/09/10)
The Ritter reaction used to be one of the most powerful synthetic tools to functionalize alcohols and nitriles, providing valuableN-alkyl amide products. However, this reaction has not been frequently used in modern organic synthesis due to its employment of strongly acidic and harsh reaction conditions, which often lead to complicated side reactions. Herein, we report the development of a new method using salts of the tropylium ion to promote the Ritter reaction. This method works well on a range of alcohol and nitrile substrates, giving the corresponding products in good to excellent yields. This reaction protocol is amenable to microwave and continuous flow reactors, offering an attractive opportunity for further applications in organic synthesis.
1,1-Diacyloxy-1-phenylmethanes as versatile N-acylating agents for amines
Chapman, Robert. S.L.,Tibbetts, Joshua. D.,Bull, Steven. D.
, p. 5330 - 5339 (2018/06/15)
1,1-Diacyloxy-1-phenylmethanes and 1-pivaloxy-1-acyloxy-1-phenylmethanes have been used as bench stable N-acylating reagents for primary and secondary amines and anilines under solvent-free conditions to afford their corresponding amides in good yield.
Umpolung Amide Synthesis using substoichiometric N-iodosuccinimide (NIS) and oxygen AS a terminal oxidant
Schwieter, Kenneth E.,Shen, Bo,Shackleford, Jessica P.,Leighty, Matthew W.,Johnston, Jeffrey N.
supporting information, p. 4714 - 4717 (2015/04/27)
Umpolung Amide Synthesis (UmAS) provides direct access to amides from an α-bromo nitroalkane and an amine. Based on its mechanistic bifurcation after convergent C-N bond formation, depending on the absence or presence of oxygen, UmAS using substoichiometric N-iodosuccinimide (NIS) under aerobic conditions has been developed. In combination with the enantioselective preparation of α-bromo nitroalkane donors, this protocol realizes the goal of enantioselective α-amino amide and peptide synthesis based solely on catalytic methods.