title: Efficient Synthesis of β-CF3/SCF3-Substituted Carbonyls via Copper-Catalyzed Electrophilic Ring-Opening Cross-Coupling of Cyclopropanols.
abstract: The first copper-catalyzed ring-opening electrophilic trifluoromethylation and trifluoromethylthiolation of cyclopropanols to form Csp3-CF3 and Csp3-SCF3 bonds have been realized. These transformations are efficient for the synthesis of β-CF3- and β-SCF3-substituted carbonyl compounds that are otherwise challenging to access. The reaction conditions are mild and tolerate a wide range of functional groups. Application to a concise synthesis of LY2409021, a glucagon receptor antagonist that is used in clinical trials for type 2 diabetes mellitus, is reported as well.
authors.affiliation: †Department of Chemistry and Center for Cancer Research, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907, United States.
authors.forename: Yong
authors.initials: Y
authors.lastname: Li
authors.affiliation: †Department of Chemistry and Center for Cancer Research, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907, United States.
authors.forename: Zhishi
authors.initials: Z
authors.lastname: Ye
authors.affiliation: †Department of Chemistry and Center for Cancer Research, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907, United States.
authors.forename: Tabitha M
authors.initials: TM
authors.lastname: Bellman
authors.affiliation: ‡Department of Chemistry, Tsinghua University, Beijing 100084, China.
authors.forename: Teng
authors.initials: T
authors.lastname: Chi
authors.affiliation: †Department of Chemistry and Center for Cancer Research, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907, United States.
authors.forename: Mingji
authors.initials: M
authors.lastname: Dai
mesh_terms: D000475:Alkenes / Q000737:chemistry; D001713:Biphenyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003924:Diabetes Mellitus, Type 2 / Q000188:drug therapy; D004988:Ethers, Cyclic / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D007454:Iodides / Q000737:chemistry*; D015394:Molecular Structure; D018027:Receptors, Glucagon / Q000037:antagonists & inhibitors*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D001713:Biphenyl Compounds; D004988:Ethers, Cyclic; D006845:Hydrocarbons, Fluorinated; D007454:Iodides; D018027:Receptors, Glucagon; C043657:cyclopropanol; C000601762:adomeglivant; D003300:Copper; C073870:cuprous iodide