Abstract
With the increasing awareness of sustainable chemistry principles, the development of an efficient and mild strategy for C(sp3)-H bond activation of nitrogen-containing compounds without the utilization of any oxidant and metal is still highly desired and challenging. Herein, we present a metal-free reaction system that enables C-H bond functionalization of aliphatic sulfonamides using DABCO as a promoter under mild conditions, affording a series of α,β-unsaturated imines in good yields with high selectivities. This protocol tolerates a broad range of functionalities and can serve as a powerful synthetic tool for the late-stage modification of complex compounds. More importantly, control experiments and detailed DFT calculations suggest that this process involves [2 + 2] cyclization/ring-cleavage reorganization, which opens up a new platform for the establishment of other related reorganization reactions.
Original language | English |
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Pages (from-to) | 4034-4040 |
Number of pages | 7 |
Journal | Chemical Science |
Volume | 12 |
Issue number | 11 |
DOIs | |
State | Published - 21 Mar 2021 |