Journal
ORGANIC LETTERS
Volume 24, Issue 31, Pages 5746-5750Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c02190
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Funding
- NIH [R35 GM125029]
- Welch Foundation [FG-2016-6568]
- Amgen
- Novartis
- Eli Lilly
- University of Texas
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In this study, we used indoles as nucleophiles in the Pd-catalyzed aza-Wacker reaction, achieving N-functionalization of indoles. By adding phthalimide ligand and Bu4NBr additive to control side reactions, high yields of the reaction were achieved.
Herein we report the use of indoles, one of the most common nitrogen-containing heterocycles in FDA-approved drugs, as nucleophiles in the Pd-catalyzed aza-Wacker reaction. This N-functionalization of indoles is a Markovnikov selective olefin functionalization of simple alkenes using catalytic Pd-(NPhth)(2)(PhCN)(2 )and O-2 as the terminal oxidant in the presence of catalytic Bu4NBr. Various substituted indoles and alkenes are found to participate; 21 examples are presented with yields ranging from 41 to 97% isolated yield. Additionally, lactams and oxazolidinones are shown to participate under the reaction conditions. Mechanistic investigations suggest that the phthalimide ligand and Bu4NBr additive slow undesired side reactions: indole decomposition and olefin isomerization, respectively.
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