Sulfoximines are commonly found in pharmaceuticals, agrochemicals and other biologically active compounds. However, limited reports exist for their selective functionalization via green and efficient protocols. Herein, we describe an electrochemical N-acylation and N-alpha-ketoacylation of sulfoximines via the selective decarboxylation and dehydration of alpha-ketoacids. These two reactions use electricity as a "traceless" oxidant and alpha-ketoacid as a selective "acyl" or "alpha-ketoacyl" source. A broad range of acylated- and alpha-ketoacylated sulfoximines were isolated in good to excellent yields (up to 88% and 96% yields). Moreover, these protocols have also been applied to late-stage derivatizations of fenofibrate and can be safely conducted on a gram scale.
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Bayer Pharma AG, Lead Discovery Berlin, Drug Discovery, Berlin, Germany
DE Shaw Res LLC, New York, NY 10036 USABayer Pharma AG, Lead Discovery Berlin, Drug Discovery, Berlin, Germany
Ayaz, Pelin
Andres, Dorothee
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Bayer Pharma AG, Lead Discovery Berlin, Drug Discovery, Berlin, GermanyBayer Pharma AG, Lead Discovery Berlin, Drug Discovery, Berlin, Germany
Andres, Dorothee
Kwiatkowski, Dennis A.
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Bayer Pharma AG, Lead Discovery Berlin, Drug Discovery, Berlin, GermanyBayer Pharma AG, Lead Discovery Berlin, Drug Discovery, Berlin, Germany
Kwiatkowski, Dennis A.
Kolbe, Carl-Christian
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Bayer Pharma AG, Lead Discovery Berlin, Drug Discovery, Berlin, GermanyBayer Pharma AG, Lead Discovery Berlin, Drug Discovery, Berlin, Germany
Kolbe, Carl-Christian
Lienau, Philip
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Bayer Pharma AG, Drug Discovery, Res Pharmacokinet, Berlin, GermanyBayer Pharma AG, Lead Discovery Berlin, Drug Discovery, Berlin, Germany
Lienau, Philip
Siemeister, Gerhard
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Bayer Pharma AG, Drug Discovery, TRG Oncol, Berlin, GermanyBayer Pharma AG, Lead Discovery Berlin, Drug Discovery, Berlin, Germany
Siemeister, Gerhard
Luecking, Ulrich
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Bayer Pharma AG, Drug Discovery, Med Chem, Berlin, GermanyBayer Pharma AG, Lead Discovery Berlin, Drug Discovery, Berlin, Germany
Luecking, Ulrich
Stegmann, Christian M.
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Bayer Pharma AG, Lead Discovery Berlin, Drug Discovery, Berlin, GermanyBayer Pharma AG, Lead Discovery Berlin, Drug Discovery, Berlin, Germany
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Westf l Wilhelms Univ Munster, Organ Chem Inst, D-48149 Munster, Germany
Weill Cornell Med, Dept Pharmacol, 413 E 69thSt, New York, NY 10021 USAWestf l Wilhelms Univ Munster, Organ Chem Inst, D-48149 Munster, Germany
Bellotti, Peter
Huang, Huan-Ming
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Weill Cornell Med, Dept Pharmacol, 413 E 69thSt, New York, NY 10021 USAWestf l Wilhelms Univ Munster, Organ Chem Inst, D-48149 Munster, Germany
Huang, Huan-Ming
Faber, Teresa
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Westf l Wilhelms Univ Munster, Organ Chem Inst, D-48149 Munster, GermanyWestf l Wilhelms Univ Munster, Organ Chem Inst, D-48149 Munster, Germany
Faber, Teresa
Glorius, Frank
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Westf l Wilhelms Univ Munster, Organ Chem Inst, D-48149 Munster, GermanyWestf l Wilhelms Univ Munster, Organ Chem Inst, D-48149 Munster, Germany
机构:
Bayer Pharma AG, Lead Discovery Berlin, Drug Discovery, Berlin, Germany
DE Shaw Res LLC, New York, NY 10036 USABayer Pharma AG, Lead Discovery Berlin, Drug Discovery, Berlin, Germany
Ayaz, Pelin
Andres, Dorothee
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h-index: 0
机构:
Bayer Pharma AG, Lead Discovery Berlin, Drug Discovery, Berlin, GermanyBayer Pharma AG, Lead Discovery Berlin, Drug Discovery, Berlin, Germany
Andres, Dorothee
Kwiatkowski, Dennis A.
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h-index: 0
机构:
Bayer Pharma AG, Lead Discovery Berlin, Drug Discovery, Berlin, GermanyBayer Pharma AG, Lead Discovery Berlin, Drug Discovery, Berlin, Germany
Kwiatkowski, Dennis A.
Kolbe, Carl-Christian
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h-index: 0
机构:
Bayer Pharma AG, Lead Discovery Berlin, Drug Discovery, Berlin, GermanyBayer Pharma AG, Lead Discovery Berlin, Drug Discovery, Berlin, Germany
Kolbe, Carl-Christian
Lienau, Philip
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h-index: 0
机构:
Bayer Pharma AG, Drug Discovery, Res Pharmacokinet, Berlin, GermanyBayer Pharma AG, Lead Discovery Berlin, Drug Discovery, Berlin, Germany
Lienau, Philip
Siemeister, Gerhard
论文数: 0引用数: 0
h-index: 0
机构:
Bayer Pharma AG, Drug Discovery, TRG Oncol, Berlin, GermanyBayer Pharma AG, Lead Discovery Berlin, Drug Discovery, Berlin, Germany
Siemeister, Gerhard
Luecking, Ulrich
论文数: 0引用数: 0
h-index: 0
机构:
Bayer Pharma AG, Drug Discovery, Med Chem, Berlin, GermanyBayer Pharma AG, Lead Discovery Berlin, Drug Discovery, Berlin, Germany
Luecking, Ulrich
Stegmann, Christian M.
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h-index: 0
机构:
Bayer Pharma AG, Lead Discovery Berlin, Drug Discovery, Berlin, GermanyBayer Pharma AG, Lead Discovery Berlin, Drug Discovery, Berlin, Germany
机构:
Westf l Wilhelms Univ Munster, Organ Chem Inst, D-48149 Munster, Germany
Weill Cornell Med, Dept Pharmacol, 413 E 69thSt, New York, NY 10021 USAWestf l Wilhelms Univ Munster, Organ Chem Inst, D-48149 Munster, Germany
Bellotti, Peter
Huang, Huan-Ming
论文数: 0引用数: 0
h-index: 0
机构:
Weill Cornell Med, Dept Pharmacol, 413 E 69thSt, New York, NY 10021 USAWestf l Wilhelms Univ Munster, Organ Chem Inst, D-48149 Munster, Germany
Huang, Huan-Ming
Faber, Teresa
论文数: 0引用数: 0
h-index: 0
机构:
Westf l Wilhelms Univ Munster, Organ Chem Inst, D-48149 Munster, GermanyWestf l Wilhelms Univ Munster, Organ Chem Inst, D-48149 Munster, Germany
Faber, Teresa
Glorius, Frank
论文数: 0引用数: 0
h-index: 0
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Westf l Wilhelms Univ Munster, Organ Chem Inst, D-48149 Munster, GermanyWestf l Wilhelms Univ Munster, Organ Chem Inst, D-48149 Munster, Germany