Journal
ORGANIC LETTERS
Volume 23, Issue 23, Pages 9100-9105Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c03389
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Funding
- NSFC [21878167, 22001144]
- Taishan Scholars Construction Projects of Shandong [tsqn201909131]
- Natural Science Foundation of Shandong Province [ZR2020QB046, ZR2020QB047, ZR2020KB007]
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This study presents a novel method for one-step construction of a polycyclic indole-3,4-fused skeleton. By involving aldehydes and hydride transfer chemistry, the challenges of constructing medium-sized rings have been successfully addressed.
A cascade aldimine condensation/1,6-hydride transfer/Mannich-type cyclization of indole-derived phenylenediamine with aldehydes was developed for one-step construction of a polycyclic indole-3,4-fused skeleton. Aldehyde serves as a key to start the whole process, including 1,6-hydride transfer enabled delta-C(sp(3))-H activation of the secondary amine. The challenges of construction of medium-sized rings are addressed via hydride transfer chemistry.
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