Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 138, Issue 16, Pages 5218-5221Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b01707
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Funding
- NBRPC (973 Program) [2015CB856600]
- NSFC [21472050, 21272075]
- 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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Comprehensive utilization of both electronic and steric properties of ligands in homogeneous gold catalysis is achieved in the regiodivergent intramolecular hydroarylation of alkynes. A flexible electron deficient phosphite ligand, combined with the readily transformable directing group methoxyl amide, is attached to a cationic Au(I) center in three-coordinate mode, affording sterically hindered ortho-position cyclization. Meanwhile, para-position cyclization is exclusively achieved with the assistance of a rigid electron-abundant phdsphine ligand-based Au(I) catalyst, in which ligands manifest the compensating effect for cyclization through steric hindrance and electronic properties. By combining gold with silver catalysts, tetrahydropyrroloquinolinones possessing a congested tricyclic structure are obtained via a proven Au/Ag relay catalytic process.
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