Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 20, Pages 9695-9706Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b01774
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Funding
- National Natural Science Foundation of China [21272078, 21572068]
- Science and Technology Planning Project of Guangdong Province, China [2014A020221035]
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Herein, we report regio- and stereoselective intramolecular direct arylations of N-(2-bromophenyl)-2-furancarboxamides 1 to produce spirooxindoles 2 and 5H-furo[2,3-c]quinolin-4-ones 3 under different reaction conditions. Specifically, in the presence of Pd(PPh3)(4) as a catalyst, PPh3 as a ligand, and K2CO3 as a base, substrates 1 underwent intramolecular alpha-arylation, possibly via a Heck insertion pathway, to provide 2, with the Zeta-isomer being favored. When the base was t-BuOLi and R-1 was an aryl group, the reaction favored Epsilon-2, possibly via an electrophilic palladation pathway. In contrast, in the presence of PdCl2 as a catalyst, (o-OMePh)(3)P as a ligand, and PivOH as an additive, substrates 1 underwent intramolecular beta-arylation to provide 3, possibly via a concerted metalation-deprotonation process.
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