Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 7, Pages 3631-3638Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b00148
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Funding
- National Natural Science Foundation of China [21572162, 21472140]
- Natural Science Foundation of Zhejiang Province [LY16B020012]
- Science and Technology Project of Zhejiang Province [2016C31022]
- Xinmiao Talent Planning Foundation of Zhejiang Province [2016R426059, 2016R426058]
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A palladium-catalyzed tandem addition/cyclization of 2-(2-aminoaryl)acetonitriles with arylboronic acids has been developed for the first time, achieving a new strategy for direct construction of indole skeletons. This system shows good functional group tolerance and remarkable chemoselectivity. In particular, the halogen (e.g., bromo and iodo) substituents are amenable to further synthetic elaborations thereby broadening the diversity of the products. Preliminary mechanistic experiments indicate that this transformation involves sequential nucleophilic addition followed by an intramolecular cydization.
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