38793-74-7Relevant academic research and scientific papers
Visible-light-induced N-heterocyclic carbene mediated cascade transformation of N-alkenoxypyridinium salts
Chen, Fei,Chen, Xiangyu,Liu, Qiang,Sheng, He,Wang, Zhixiang
, (2022/02/02)
While N-alkenoxypyridinium salts are widely used for the synthesis of α-functionalized ketones via umpolung strategy, such approaches are usually limited to special nucleophiles at high temperatures. Herein, we developed an alternative photoinduced N-heterocyclic carbene (NHC)- mediated functionalization of N-alkenoxypyridinium salts with various nucleophiles, including tetramethylammonium azide, secondary amines, aryl and alkyl thiols, and even the challenging C(sp3)-nucleophiles, under mild conditions. A cascade radical-radical coupling/nucleophilic substitution sequence was proposed, wherein the NHC enabled the formation of a photoactive electron donor-acceptor complex for α-iodo ketone synthesis.
