title: Simple sulfinate synthesis enables C-H trifluoromethylcyclopropanation.
abstract: A simple method to convert readily available carboxylic acids into sulfinate salts by employing an interrupted Barton decarboxylation reaction is reported. A medicinally oriented panel of ten new sulfinate reagents was created using this method, including a key trifluoromethylcyclopropanation reagent, TFCS-Na. The reactivity of six of these salts towards C-H functionalization was field-tested using several different classes of heterocycles.
authors.affiliation: Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA).
authors.forename: Ryan
authors.initials: R
authors.lastname: Gianatassio
authors.forename: Shuhei
authors.initials: S
authors.lastname: Kawamura
authors.forename: Cecil L
authors.initials: CL
authors.lastname: Eprile
authors.forename: Klement
authors.initials: K
authors.lastname: Foo
authors.forename: Jason
authors.initials: J
authors.lastname: Ge
authors.forename: Aaron C
authors.initials: AC
authors.lastname: Burns
authors.forename: Michael R
authors.initials: MR
authors.lastname: Collins
authors.forename: Phil S
authors.initials: PS
authors.lastname: Baran
mesh_terms: D000147:Acids, Heterocyclic; D002384:Catalysis; D008958:Models, Molecular; D015394:Molecular Structure; D013441:Sulfinic Acids / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D000147:Acids, Heterocyclic; D013441:Sulfinic Acids
keywords: CH functionalization; analogue synthesis; bioisosteres; heterocycles; sulfinate salts
references.citation: Org Lett. 2012 Oct 5;14(19):4979-81
references.pmid: 22984900
references.citation: Bioorg Med Chem Lett. 2003 Oct 20;13(20):3541-4
references.pmid: 14505666
references.citation: Angew Chem Int Ed Engl. 2014 Apr 22;53(17):4404-7
references.pmid: 24652820
references.citation: Org Lett. 2013 Jan 18;15(2):406-9
references.pmid: 23305217
references.citation: J Med Chem. 2008 Apr 10;51(7):2115-27
references.pmid: 18335976
references.citation: J Med Chem. 2014 Feb 27;57(4):1616-20
references.pmid: 24472070
references.citation: Bioorg Med Chem Lett. 2011 Sep 15;21(18):5274-82
references.pmid: 21803580
references.citation: ACS Med Chem Lett. 2013 Apr 22;4(6):514-6
references.pmid: 24900702
references.citation: J Am Chem Soc. 2013 Sep 4;135(35):12994-7
references.pmid: 23957305
references.citation: Org Lett. 2011 Apr 1;13(7):1852-5
references.pmid: 21391555
references.citation: J Med Chem. 2014 Jun 26;57(12):5085-93
references.pmid: 24673739
references.citation: Bioorg Med Chem Lett. 2003 Mar 24;13(6):1051-4
references.pmid: 12643909
references.citation: J Med Chem. 2012 Mar 8;55(5):1868-97
references.pmid: 22320327
references.citation: Angew Chem Int Ed Engl. 2013 Apr 2;52(14):3949-52
references.pmid: 23460402
references.citation: Nature. 2012 Dec 6;492(7427):95-9
references.pmid: 23201691
references.citation: J Am Chem Soc. 2012 Jan 25;134(3):1494-7
references.pmid: 22229949
references.citation: J Org Chem. 2013 May 3;78(9):4615-9
references.pmid: 23594305
references.citation: Proc Natl Acad Sci U S A. 2011 Aug 30;108(35):14411-5
references.pmid: 21844378