title: Rhodium(III)-catalyzed indazole synthesis by C-H bond functionalization and cyclative capture.
abstract: An efficient, one-step, and highly functional group-compatible synthesis of substituted N-aryl-2H-indazoles is reported via the rhodium(III)-catalyzed C-H bond addition of azobenzenes to aldehydes. The regioselective coupling of unsymmetrical azobenzenes was further demonstrated and led to the development of a new removable aryl group that allows for the preparation of indazoles without N-substitution. The 2-aryl-2H-indazole products also represent a new class of readily prepared fluorophores for which initial spectroscopic characterization has been performed.
authors: Department of Chemistry, Yale University, New Haven, Connecticut 06520, USA.
authors: Yajing
authors: Y
authors: Lian
authors: Robert G
authors: RG
authors: Bergman
authors: Luke D
authors: LD
authors: Lavis
authors: Jonathan A
authors: JA
authors: Ellman
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D001391:Azo Compounds / Q000737:chemistry; D002384:Catalysis; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D007191:Indazoles / Q000138:chemical synthesis* / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D001391:Azo Compounds; D005456:Fluorescent Dyes; D007191:Indazoles; D012238:Rhodium; C009850:azobenzene
references: ACS Chem Biol. 2008 Mar 20;3(3):142-55
references: 18355003
references: Org Lett. 2010 Jun 18;12(12):2884-7
references: 20507088
references: Chem Soc Rev. 2011 Sep;40(9):4740-61
references: 21666903
references: Chem Rev. 2000 May 10;100(5):1847-1874
references: 11777423
references: J Am Chem Soc. 2012 Jan 25;134(3):1482-5
references: 22257031
references: J Med Chem. 2005 Feb 24;48(4):1132-44
references: 15715479
references: Angew Chem Int Ed Engl. 2009;48(37):6879-82
references: 19681082
references: Chem Soc Rev. 2007 Jul;36(7):1173-93
references: 17576484
references: J Am Chem Soc. 2011 Aug 3;133(30):11430-3
references: 21714533
references: Chem Sci. 2012 Jan 1;3(10):3088-3092
references: 23050074
references: Chem Commun (Camb). 2011 Nov 28;47(44):12074-6
references: 22006288
references: Angew Chem Int Ed Engl. 2012 Nov 19;51(47):11819-23
references: 23086779
references: Chemistry. 2011 Nov 4;17(45):12591-5
references: 21972033
references: Org Lett. 2011 Aug 19;13(16):4390-3
references: 21793534
references: Chemistry. 2010 Oct 4;16(37):11212-22
references: 20740508
references: J Am Chem Soc. 2012 Dec 5;134(48):19592-5
references: 23146122
references: Org Lett. 2012 Jan 20;14(2):636-9
references: 22229857
references: Angew Chem Int Ed Engl. 2012 Sep 3;51(36):8960-9009
references: 22887739
references: Chem Rev. 2010 Feb 10;110(2):624-55
references: 19438203
references: Chem Soc Rev. 2011 Aug;40(8):4422-37
references: 21483974
references: Org Lett. 2012 May 4;14(9):2304-7
references: 22500854
references: Org Lett. 2013 Feb 1;15(3):620-3
references: 23343496
references: Chem Rev. 2002 Nov;102(11):4139-75
references: 12428986
references: J Am Chem Soc. 2004 Mar 3;126(8):2300-1
references: 14982422
references: Science. 2012 Oct 26;338(6106):500-3
references: 23112327
references: Org Lett. 2011 Jul 1;13(13):3542-5
references: 21644532
references: Angew Chem Int Ed Engl. 2013 Feb 25;52(9):2577-80
references: 23364931
references: Angew Chem Int Ed Engl. 2013 Jan 7;52(2):629-33
references: 23172703
references: Chem Commun (Camb). 2012 May 25;48(42):5163-5
references: 22514045
references: Mini Rev Med Chem. 2012 Oct;12(12):1293-300
references: 23092440
references: J Am Chem Soc. 2013 Jan 9;135(1):66-9
references: 23244023
references: Prog Mol Biol Transl Sci. 2013;113:1-34
references: 23244787
references: Angew Chem Int Ed Engl. 2011 Feb 25;50(9):2115-9
references: 21344564
references: Chem Commun (Camb). 2011 Sep 28;47(36):10133-5
references: 21826369
references: Chemistry. 2013 Apr 8;19(15):4701-6
references: 23460480
references: Angew Chem Int Ed Engl. 2012 Jul 16;51(29):7318-22
references: 22514051
references: Chem Rev. 2010 Feb 10;110(2):1147-69
references: 20078038
references: Angew Chem Int Ed Engl. 2009;48(28):5094-115
references: 19557755
references: Chem Soc Rev. 2012 May 7;41(9):3651-78
references: 22377832
references: Org Lett. 2012 Sep 7;14(17):4498-501
references: 22892028
references: J Am Chem Soc. 2011 Feb 9;133(5):1248-50
references: 21204527
references: Science. 2012 Oct 26;338(6106):504-6
references: 23112328
references: Proc Natl Acad Sci U S A. 2000 Jul 5;97(14):7754-9
references: 10869434
references: Org Lett. 2012 Feb 3;14(3):906-9
references: 22263914