Journal
ACS CATALYSIS
Volume 6, Issue 2, Pages 798-808Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.5b01971
Keywords
DFT; difunctionalization; gold; photoredox; cyclization
Categories
Funding
- NSFC [21202006, 21325208, 21172209, 21361140372]
- 973 Program [2012CB215306]
- FRFCU [WK2060190025, WK2060190040, FRF-TP-14-015A2]
- CAS [KJCX2-EW-J02]
- PCSIRT
- National Supercomputing Center in Shenzhen
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A systematic theoretical study has been carried out on the visible light-mediated gold-catalyzed oxyarylation of alkenes. The detailed mechanism of the dual Au and photoredox-catalyzed difunctionalization, including both the photoredox and gold catalytic cycles, has been investigated. The calculation results show that the oxidative quenching of the photoredox catalyst is more favorable than reductive quenching. The favorable gold catalytic cycle is the sequence of radical addition, single electron transfer (SET), coordination, cyclization, and reductive elimination. The facility of the favorable mechanism is determined by two factors: First, both oxidation steps (i.e., radical addition and SET) occur prior to the cyclization step to generate the feasible cyclization precursor of the Au(III) complex. Second, the radical addition formally increases the electron density on the gold center and thus favors the radical addition followed by SET sequence.
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