title: Orchestrated triple C-H activation reactions using two directing groups: rapid assembly of complex pyrazoles.
abstract: A sequential triple C-H activation reaction directed by a pyrazole and an amide group leads to the well-controlled construction of sterically congested dihydrobenzo[e]indazole derivatives. This cascade reaction demonstrates that the often problematic competing C-H activation pathways in the presence of multiple directing groups can be harvested by design to improve step economy in synthesis. Pyrazole as a relatively weak coordinating group is shown to direct Csp3-H activation for the first time.
authors: Department of Chemistry, The Scripps Research Institute (TSRI), 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA).
authors: Weibo
authors: W
authors: Yang
authors: Shengqing
authors: S
authors: Ye
authors: Dewey
authors: D
authors: Fanning
authors: Timothy
authors: T
authors: Coon
authors: Yvonne
authors: Y
authors: Schmidt
authors: Paul
authors: P
authors: Krenitsky
authors: Dean
authors: D
authors: Stamos
authors: Jin-Quan
authors: JQ
authors: Yu
mesh_terms: D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D006859:Hydrogen / Q000737:chemistry; D010165:Palladium; D011720:Pyrazoles / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D011720:Pyrazoles; D010165:Palladium; D002244:Carbon; D006859:Hydrogen
keywords: CH activation; benzo[e]indazoles; cascade reactions; pyrazole
references: Chem Soc Rev. 2011 Oct;40(10):5068-83
references: 21643614
references: Angew Chem Int Ed Engl. 2011 Feb 7;50(6):1380-3
references: 21290517
references: Chem Soc Rev. 2011 Oct;40(10):4902-11
references: 21505712
references: Angew Chem Int Ed Engl. 2013 May 10;52(20):5386-9
references: 23576316
references: Angew Chem Int Ed Engl. 2013 Nov 4;52(45):11726-43
references: 24105797
references: J Am Chem Soc. 2007 Mar 28;129(12):3510-1
references: 17335217
references: Chem Soc Rev. 2007 Jul;36(7):1173-93
references: 17576484
references: Chem Rev. 2010 Feb 10;110(2):1147-69
references: 20078038
references: J Am Chem Soc. 2008 Oct 29;130(43):14058-9
references: 18834119
references: Angew Chem Int Ed Engl. 2009;48(52):9792-826
references: 19998294
references: Angew Chem Int Ed Engl. 2012 Nov 12;51(46):11561-5
references: 23055447
references: Exp Appl Acarol. 2005;36(3):177-85
references: 16132732
references: Chem Lett. 2011;40(9):1004-1006
references: 23637469
references: Angew Chem Int Ed Engl. 2013 Nov 18;52(47):12385-9
references: 24105995
references: Acc Chem Res. 2009 Aug 18;42(8):1074-86
references: 19552413
references: J Am Chem Soc. 2014 Mar 26;136(12):4780-7
references: 24593822
references: J Org Chem. 2004 Jun 25;69(13):4433-40
references: 15202898
references: J Am Chem Soc. 2008 Oct 8;130(40):13285-93
references: 18781752
references: Angew Chem Int Ed Engl. 2006 Apr 10;45(16):2619-22
references: 16544353
references: J Am Chem Soc. 2013 Jul 24;135(29):10630-3
references: 23822812
references: Angew Chem Int Ed Engl. 2009;48(28):5094-115
references: 19557755
references: J Am Chem Soc. 2010 Jun 30;132(25):8569-71
references: 20524609
references: Eur J Med Chem. 2013 Nov;69:735-53
references: 24099993