期刊
ACS CATALYSIS
卷 11, 期 11, 页码 6633-6642出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.1c01222
关键词
C(sp(3))-O/N cross-couplings; photoredox catalysis; copper; iodine; density functional calculations
资金
- NSFC [21773025]
- China Postdoctoral Science Foundation [2019M651184]
- Fundamental Research Funds for the Central Universities [2412019QD007]
Photocatalytic coupling reactions have rapidly developed in the field of organic synthesis. A novel metallaphotoredox catalysis utilizing a NaI-PPh3 photoredox catalyst and Cu(I) catalyst was designed and evaluated, achieving high yields of C(sp(3))-O/N cross-couplings of alkyl N-hydroxyphthalimide esters with phenols/secondary amines under mild conditions with only blue light irradiation. This strategy provides a facile and economic route for C(sp(3))-X cross-coupling reactions while also offering a clear mechanistic understanding.
Photocatalytic coupling reactions have developed rapidly in the field of organic synthesis. However, highly efficient, broad-spectrum, low-cost, and energy-saving catalytic systems are urgently needed. Herein a desirable alternative combining NaI-PPh3 photoredox catalyst and Cu(I) catalyst was theoretically designed and evaluated from photophysical processes and potential energy surfaces. This metallaphotoredox catalysis could achieve C(sp(3))-O/N cross-couplings of alkyl N-hydroxyphthalimide esters with phenols/secondary amines via a radical mechanism merging photoexcited radical decarboxylation and a low-valent Cu-I-Cu-II-Cu-I cycle. More importantly, a series of target reactions can be realized with high yield (>= 90%) at room temperature under only irradiation with 10 W blue light-emitting diodes for 4 h without additional precious photocatalysts, which is mild, convenient, and environmentally friendly. Thus, this synthesis strategy combining theory and experiment can provide a facile and economic route and a clear mechanistic understanding for C(sp(3))-X cross-coupling reactions.
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