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Rapid Dehydroxytrifluoromethoxylation of Alcohols

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Presentation on theme: "Rapid Dehydroxytrifluoromethoxylation of Alcohols"— Presentation transcript:

1 Rapid Dehydroxytrifluoromethoxylation of Alcohols
Wei Zhang, Jia Chen, Jin-Hong Lin, Ji-Chang Xiao, Yu-Cheng Gu  iScience  Volume 5, Pages (July 2018) DOI: /j.isci Copyright © 2018 The Author(s) Terms and Conditions

2 iScience 2018 5, 110-117DOI: (10.1016/j.isci.2018.07.004)
Copyright © 2018 The Author(s) Terms and Conditions

3 Figure 1 31P NMR Spectra of the Ph3P/ICH2CH2I Reaction System
iScience 2018 5, DOI: ( /j.isci ) Copyright © 2018 The Author(s) Terms and Conditions

4 Scheme 1 Trifluoromethoxylation Protocols
iScience 2018 5, DOI: ( /j.isci ) Copyright © 2018 The Author(s) Terms and Conditions

5 Scheme 2 Dehydroxytrifluoromethoxylation of Alcohols
Isolated yields. Reaction conditions: alcohol 1 (0.5 mmol), AgOCF3 (2.0 mmol), Ph3P (0.7 mmol), ICH2CH2I (0.7 mmol), DMF (3 mL), 80°C, 15 min, N2 atmosphere. The yield of product 3a was determined by 19F NMR spectroscopy. See also Figures S1–S60. iScience 2018 5, DOI: ( /j.isci ) Copyright © 2018 The Author(s) Terms and Conditions

6 Scheme 3 Dehydroxytrifluoromethoxylation of Alkyl Alcohols
Isolated yields. Reaction conditions: alcohol 1 (0.5 mmol), AgOCF3 (2.0 mmol), Ph2PCH=CH2 (1.3 mmol), ICH2CH2I (0.6 mmol), DMF (3 mL), 100°C, 15 min, N2 atmosphere. The yield of product 3i was determined by 19F NMR spectroscopy. See also Figures S61–S88. iScience 2018 5, DOI: ( /j.isci ) Copyright © 2018 The Author(s) Terms and Conditions

7 Scheme 4 The Formation of Key Intermediates
iScience 2018 5, DOI: ( /j.isci ) Copyright © 2018 The Author(s) Terms and Conditions

8 Scheme 5 Trifluoromethoxylation of 18O-Labeled Alcohol
The isolated yield was calculated based on Ph3P as the limiting reagent. See also Figures S89 and S90. iScience 2018 5, DOI: ( /j.isci ) Copyright © 2018 The Author(s) Terms and Conditions

9 Scheme 6 The Plausible Reaction Mechanism
iScience 2018 5, DOI: ( /j.isci ) Copyright © 2018 The Author(s) Terms and Conditions

10 Scheme 7 The R3P/I2 System-Promoted Dehydroxytrifluoromethoxylation
The yields of 2a and 3a were determined by 19F NMR spectroscopy. iScience 2018 5, DOI: ( /j.isci ) Copyright © 2018 The Author(s) Terms and Conditions


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