Journal
ACS CATALYSIS
Volume 9, Issue 3, Pages 1888-1894Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.8b05054
Keywords
beta-C-H functionalization; site selectivity; dioxygen; rearrangement; gram-scale synthesis
Categories
Funding
- National Natural Science Foundation of China [21390402, 21520102003]
- 973 Program [2012CB725302]
- CAS Interdisciplinary Innovation Team
Ask authors/readers for more resources
Site-selective intermolecular C-H bond functionalization is of central importance to synthetic chemistry. In particular, direct beta-functionalization of N-heterocycles still remains a great challenge. Herein, we develop a strategy for oxidation-induced thiolation and selenation at the beta-position of piperidine derivatives and 1,2,3,4-tetrahydroisoquinoline via C-H bond functionalization. Various 4-sulfenylisoquinolines, 3-sulfenylpyridines, and 4-selenylisoquinolines can be obtained by using O-2 as the only oxidant. Notably, neither a directing group nor a metal catalyst is necessary in this transformation. The preliminary mechanistic studies revealed that the oxidation and rearrangement pathway were key steps in this transformation, which provides a meaningful strategy for controlling site selectivity in the beta-functionalization of N-heterocycles.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available