Visible Light-Induced Aerobic Epoxidation of α,β-Unsaturated Ketones Mediated by Amidines

Article abstract of DOI:10.1021/acs.joc.8b01710

An aerobic photoepoxidation of α,β-unsaturated ketones driven by visible light in the presence of tetramethylguanidine (3b), tetraphenylporphine (H₂TPP), and molecular oxygen under mild conditions was revealed. The corresponding α,β-epoxy ketones were obtained in yields of up to 94% in 96 h. The reaction time was shortened to 4.6 h by flow synthesis. The mechanism related to singlet oxygen was supported by experiments and density functional theory (DFT) calculations.

Full text of DOI:10.1021/acs.joc.8b01710

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Article
Visible Light Induced Aerobic Epoxidation of #,#-
Unsaturated Ketones Mediated by Amidines
Yufeng Wu, Guangli Zhou, Qingwei Meng, Xiaofei Tang, Guangzhi
Liu, Hang Yin, Jingnan Zhao, Fan Yang, Zongyi Yu, and Yi Luo
J. Org. Chem., Just Accepted Manuscript • DOI: 10.1021/acs.joc.8b01710 • Publication Date (Web): 04 Oct 2018
Downloaded from http://pubs.acs.org on October 4, 2018
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Visible Light Induced Aerobic Epoxidation of α,β-Unsaturated Ketones
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INTRODUCTION
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RESULTS AND DISCUSSION
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CONCLUSIONS
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EXPERIMENTAL SECTION
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C
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Total residence time = Total time × 0.21
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,
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훷ref
훷PS
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PS
×
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ref
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CALCULATION SECTION
ɛ
V1
Total residence time = N ×
Total time = N ×
푣푙푖푞,푅 + 푣푔푎푠,푅
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ASSOCIATED CONTENT
푣푙푖푞,푅
Supporting Information
V1
푣푙푖푞,푅
Total residence time = Total time ×
×
V2 푣푙푖푞,푅 + 푣푔푎푠,푅
푣푙푖푞,푅
푣푔푎푠,푅
푣푙푖푞,푅 = 1.00
푣푔푎푠,푅 = 1.0
V1
V1 =
8.4 mL V2
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AUTHORS INFORMATION
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ACKNOWLEDGMENTS
REFERENCES
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