Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 49, Pages 14960-14964Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201508340
Keywords
acridones; arynes; ligand control; multicomponent reactions; phenanthridinones
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Funding
- NBRPC 973 Program [2015CB856600]
- NSFC [21472050, 21272075]
- NCET [120178]
- DFMEC [20130076110023]
- Fok Ying Tung Education Foundation [141011]
- program for Shanghai Rising Star [15QA1401800]
- Professor of Special Appointment (Eastern Scholar) at Shanghai Institutions of Higher Learning
- Changjiang Scholar and Innovative Research Team in University
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A palladium-catalyzed regiodivergent C-1 insertion multicomponent reaction involving aryne, CO, and 2-iodoaniline is established to construct the scaffolds of phenanthridinone and acridone alkaloids. Regioselective control is achieved under the guidance of selective ligands. The phenanthridinones are solely obtained under ligand-free condition. In comparison, application of the electron-abundant bidentate ligand dppm afforded the acridones with high efficiency. The release rate of the aryne from the precursor assists the regioselectivity of insertion as well, which was revealed through interval NMR tracking. A plausible mechanism was suggested based on the control experiments. Representative natural products and two types of natural product analogues were synthesized divergently through this tunable method.
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