Synthesis of acyl fluorides via photocatalytic fluorination of aldehydic C-H bonds
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Meanwell, Michael
[1
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Lehmann, Johannes
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Simon Fraser Univ, Dept Chem, Burnaby, BC V5A 1S6, CanadaSimon Fraser Univ, Dept Chem, Burnaby, BC V5A 1S6, Canada
Lehmann, Johannes
[1
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Eichenberger, Marc
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F Hoffmann La Roche Ltd, Roche Innovat Ctr Basel, Roche Pharma Res & Early Dev pRED, Med Chem, Grenzacherstr 124, CH-4070 Basel, SwitzerlandSimon Fraser Univ, Dept Chem, Burnaby, BC V5A 1S6, Canada
Eichenberger, Marc
[2
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Martin, Rainer E.
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F Hoffmann La Roche Ltd, Roche Innovat Ctr Basel, Roche Pharma Res & Early Dev pRED, Med Chem, Grenzacherstr 124, CH-4070 Basel, SwitzerlandSimon Fraser Univ, Dept Chem, Burnaby, BC V5A 1S6, Canada
Martin, Rainer E.
[2
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Britton, Robert
[1
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[1] Simon Fraser Univ, Dept Chem, Burnaby, BC V5A 1S6, Canada
[2] F Hoffmann La Roche Ltd, Roche Innovat Ctr Basel, Roche Pharma Res & Early Dev pRED, Med Chem, Grenzacherstr 124, CH-4070 Basel, Switzerland
Acyl fluorides are versatile acylating agents owing to their unique stability. Their synthesis, however, can present challenges and is typically accomplished through deoxyfluorination of carboxylic acids. Here, we demonstrate that acyl fluorides can be prepared directly from aldehydes via a C(sp(2))-H fluorination reaction involving the inexpensive photocatalyst sodium decatungstate and electrophilic fluorinating agent N-fluorobenzenesulfonimide. This convenient fluorination strategy enables direct conversion of aliphatic and aromatic aldehydes into acylating agents.
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Simon Fraser Univ, Dept Chem, Burnaby, BC V5A 1S6, CanadaSimon Fraser Univ, Dept Chem, Burnaby, BC V5A 1S6, Canada
Halperin, Shira D.
Fan, Hope
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Simon Fraser Univ, Dept Chem, Burnaby, BC V5A 1S6, CanadaSimon Fraser Univ, Dept Chem, Burnaby, BC V5A 1S6, Canada
Fan, Hope
Chang, Stanley
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Simon Fraser Univ, Dept Chem, Burnaby, BC V5A 1S6, CanadaSimon Fraser Univ, Dept Chem, Burnaby, BC V5A 1S6, Canada
Chang, Stanley
Martin, Rainer E.
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F Hoffmann Roche AG, Med Chem Small Mol Res Pharma Res & Early Dev pRE, CH-4070 Basel, SwitzerlandSimon Fraser Univ, Dept Chem, Burnaby, BC V5A 1S6, Canada
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Simon Fraser Univ, Dept Chem, Burnaby, BC V5A 1S6, CanadaSimon Fraser Univ, Dept Chem, Burnaby, BC V5A 1S6, Canada
Nodwell, Matthew B.
Bagai, Abhimanyu
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Simon Fraser Univ, Dept Chem, Burnaby, BC V5A 1S6, CanadaSimon Fraser Univ, Dept Chem, Burnaby, BC V5A 1S6, Canada
Bagai, Abhimanyu
Halperin, Shira D.
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Simon Fraser Univ, Dept Chem, Burnaby, BC V5A 1S6, CanadaSimon Fraser Univ, Dept Chem, Burnaby, BC V5A 1S6, Canada
Halperin, Shira D.
Martin, Rainer E.
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F Hoffmann La Roche Ltd, Roche Pharma Res & Early Dev, Roche Innovat Ctr Basel, Mol Design & Chem Biol, CH-4070 Basel, SwitzerlandSimon Fraser Univ, Dept Chem, Burnaby, BC V5A 1S6, Canada
Martin, Rainer E.
Knust, Henner
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F Hoffmann La Roche Ltd, Roche Pharma Res & Early Dev, Med Chem, Roche Innovat Ctr Basel, CH-4070 Basel, SwitzerlandSimon Fraser Univ, Dept Chem, Burnaby, BC V5A 1S6, Canada
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Taiyuan Univ Technol, Coll Chem, Taiyuan 030024, Shanxi, Peoples R ChinaTaiyuan Univ Technol, Coll Chem, Taiyuan 030024, Shanxi, Peoples R China
Guo, Yunfei
Qi, Jipeng
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Taiyuan Univ Technol, Coll Chem, Taiyuan 030024, Shanxi, Peoples R ChinaTaiyuan Univ Technol, Coll Chem, Taiyuan 030024, Shanxi, Peoples R China
Qi, Jipeng
Guo, Hongyu
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Taiyuan Univ Technol, Coll Chem, Taiyuan 030024, Shanxi, Peoples R ChinaTaiyuan Univ Technol, Coll Chem, Taiyuan 030024, Shanxi, Peoples R China
Guo, Hongyu
Liu, Rongfang
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Shanxi Univ Chinese Med, Coll Tradit Chinese Med & Food Engn, Jinzhong 030619, Shanxi, Peoples R ChinaTaiyuan Univ Technol, Coll Chem, Taiyuan 030024, Shanxi, Peoples R China
Liu, Rongfang
Zhou, Rong
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Taiyuan Univ Technol, Coll Chem, Taiyuan 030024, Shanxi, Peoples R China
Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R ChinaTaiyuan Univ Technol, Coll Chem, Taiyuan 030024, Shanxi, Peoples R China