N -Chlorosulfonyl carbamate-enabled, photoinduced amidation of quinoxalin-2(1 H )-ones.
Chu-Ping YuanZhen-Zhen XieYu ZhengJun-Tao HeJian-Ping GuanHong-Bin ChenHao-Yue XiangKai ChenJun-An XiaoPublished in: Chemical communications (Cambridge, England) (2023)
Reported herein is the design and development of a new photo-induced amidation protocol with the readily available N -chlorosulfonyl carbamate as an effective amidyl-radical precursor, which could be readily prepared from commercial low-cost chlorosulfonyl isocyanate (CSI) and alcohol feedstocks. The synthetic potency of this developed protocol was well demonstrated by direct amidation of various quinoxalin-2(1 H )-ones. The protocol could be further streamlined by implementing a one-pot/two-step/three-component process of CSI, alcohol, and quinoxalin-2(1 H )-one, with significantly improved reaction efficiency. This methodology offers an intriguing opportunity for rapid expansion of nitrogen-containing molecular complexity, thus inspiring comprehensive exploration of a new reaction mode of CSI reagent.