Cobalt-Catalyzed Hydrogen-Bond-Promoted Tandem Cyclization and Oxygen Migration: Access to Sterically Congested Fused Tetrahydro-β-Carbolines
Yutian Zhou1,2, Jian-Dong Zhang1,2, Jiacheng Xu1,2, You Zi(訾由)3*, Shun-Jun Ji(纪顺俊)1,2*, Xiao-Ping Xu(徐小平)1,2,4*
1Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, P. R. China
2Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou 215123, P. R. China
3School of Chemistry and Chemical Engineering, Nantong University, Nantong 226019, P. R. China
4Innovation Center for Chemical Science, Soochow University, Suzhou 215123, P. R. China
Org. Lett. 2026, 28, 5068–5074
Abstract: A cobalt-catalyzed, hydrogen-bond-promoted strategy for the synthesis of sterically congested fused tetrahydro-beta-carbolines bearing quaternary carbon centers is reported. This transformation employs tryptamine-derived isocyanides and anthranils as readily available building blocks and proceeds through a tandem oxygen migration and cyclization process with high atom economy. Moderate to good yields are obtained for structurally diverse products. Water plays a crucial role by providing a hydrogen-bonding environment and serving as a proton shuttle to facilitate the reaction process, which is supported by isotope-labeling experiments and DFT calculations.
Article information: https://doi.org/10.1021/acs.orglett.6c00724