Addition of a carbene catalyst to indole aryl aldehyde activates a remote δ-sp2 carbon for protonation and formal [4+2] reaction

• Main Authors: Zheng, Pengcheng, Wu, Shuquan, Mou, Chengli, Xue, Wei, Jin, Zhichao, Chi, Robin Yonggui
• Other Authors: School of Physical and Mathematical Sciences
• Format: Article
• Language: English
• Published: 2020
• Subjects: Science::Chemistry::Organic chemistry; Carbene Catalyst; Breslow Intermediate
• Online Access: https://hdl.handle.net/10356/137753
• Institution: Nanyang Technological University

The addition of a carbene catalyst to an indole aryl aldehyde leads to the activation of a remote sp2 carbon that is five atoms away from the catalyst. The unsaturated Breslow intermediate formed between the catalyst and substrate undergoes an internal redox reaction and remote carbon protonation to...