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Title: Rhodium(III)-Catalyzed Indazole Synthesis by C–H Bond Functionalization and Cyclative Capture

Journal Article · · Journal of the American Chemical Society
DOI: https://doi.org/10.1021/ja402761p · OSTI ID:1123335
 [1];  [2];  [3];  [1]
  1. Department of Chemistry, Yale University, New Haven, Connecticut 06520, United States
  2. Division of Chemical Sciences, Lawrence Berkeley National Laboratory, and Department of Chemistry, University of California, Berkeley, California 94720, United States
  3. Janelia Farm Research Campus, Howard Hughes Medical Institute, Ashburn, Virginia 20147, United States
+ Show Author Affiliations

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Sponsoring Organization:
USDOE
OSTI ID:
1123335
Journal Information:
Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 19 Vol. 135; ISSN 0002-7863
Publisher:
American Chemical SocietyCopyright Statement
Country of Publication:
United States
Language:
English

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Grignard‐Type Arylation of Aldehydes via a Rhodium‐Catalyzed CH Activation under Mild Conditions journal May 2011
A Novel Rhodium‐Catalyzed Cascade Cyclization: Direct Synthesis of 3‐Substituted Phthalides from Aldehydes and Aromatic Acids journal October 2012
Palladium‐Catalyzed Regioselective Halogenation of Aromatic Azo Compounds journal January 2013
Rhodium‐Catalyzed Direct Addition of Indoles to N‐Sulfonylaldimines journal January 2013
Palladium(II)-Catalyzed CH Activation/CC Cross-Coupling Reactions: Versatility and Practicality journal June 2009
A General and Mild Palladium‐Catalyzed Domino Reaction for the Synthesis of 2H‐Indazoles journal August 2009
Rhodium‐Catalyzed Direct Addition of Aryl CH Bonds to N‐Sulfonyl Aldimines journal January 2011
Mild Rhodium(III)‐Catalyzed CH Activation and Intermolecular Annulation with Allenes journal April 2012
CH Bond Functionalization: Emerging Synthetic Tools for Natural Products and Pharmaceuticals journal August 2012
Rhodium(III)‐Catalyzed Oxidative CH Functionalization of Azomethine Ylides journal October 2012
Rhodium(III)‐Catalyzed Alkenyl CH Bond Functionalization: Convergent Synthesis of Furans and Pyrroles journal November 2012
Rhodium(III)-Catalyzed CC Coupling between Arenes and Aziridines by CH Activation journal January 2013
Functional Near‐Infrared Fluorescent Probes journal February 2008
Oxidative Coupling of Aromatic Substrates with Alkynes and Alkenes under Rhodium Catalysis journal August 2010
Rhodium‐Catalyzed Annulation of N‐Benzoylsulfonamide with Isocyanide through CH Activation journal October 2011
Rhodium(III)‐Catalyzed Amidation of Aryl Ketone O‐Methyl Oximes with Isocyanates by CH Activation: Convergent Synthesis of 3‐Methyleneisoindolin‐1‐ones journal March 2013
The Chemistry of Small-Molecule Fluorogenic Probes book January 2013
The ruthenium-catalyzed silylation of aromatic CH bonds with triethylsilane journal November 2003
Bright Ideas for Chemical Biology journal March 2008
Rhodium-Catalyzed C−C Bond Formation via Heteroatom-Directed C−H Bond Activation journal February 2010
Palladium-Catalyzed Ligand-Directed C−H Functionalization Reactions journal February 2010
Photoinduced Motions in Azo-Containing Polymers journal November 2002
Photoalignment of Liquid-Crystal Systems journal May 2000
The Preparation of Cyclopentadienyl [ o -(Phenylazo)Phenyl]Nickel journal May 1963
The Reaction of Azobenzene and Carbon Monoxide journal September 1956
A Highly Selective Catalytic Method for the Oxidative Functionalization of C−H Bonds journal March 2004
Rhodium(III)-Catalyzed Arylation of Boc-Imines via C−H Bond Functionalization journal January 2011
Expedient Synthesis of N-Acyl Anthranilamides and β-Enamine Amides by the Rh(III)-Catalyzed Amidation of Aryl and Vinyl C–H Bonds with Isocyanates journal July 2011
Mechanism of the Rhodium(III)-Catalyzed Arylation of Imines via C–H Bond Functionalization: Inhibition by Substrate
  • Tauchert, Michael E.; Incarvito, Christopher D.; Rheingold, Arnold L.
  • Journal of the American Chemical Society, Vol. 134, Issue 3 https://doi.org/10.1021/ja211110h
journal January 2012
Rh(III)-Catalyzed Regioselective Synthesis of Pyridines from Alkenes and α,β-Unsaturated Oxime Esters journal December 2012
Indazole Estrogens:  Highly Selective Ligands for the Estrogen Receptor β journal January 2005
Intramolecular Fe(II)-Catalyzed N−O or N−N Bond Formation from Aryl Azides journal May 2010
Consecutive Condensation, C–N and N–N Bond Formations: A Copper- Catalyzed One-Pot Three-Component Synthesis of 2H-Indazole journal June 2011
Rhodium-Catalyzed Oxidative ortho-Acylation of Benzamides with Aldehydes: Direct Functionalization of the sp2 C–H Bond journal July 2011
N-Directing Group Assisted Rhodium-Catalyzed Aryl C–H Addition to Aryl Aldehydes journal January 2012
Tandem Rh(III)-Catalyzed Oxidative Acylation of Secondary Benzamides with Aldehydes and Intramolecular Cyclization: The Direct Synthesis of 3-Hydroxyisoindolin-1-ones journal January 2012
Rhodium-Catalyzed Synthesis of Branched Amines by Direct Addition of Benzamides to Imines journal April 2012
Olefinic C–H Bond Addition to Aryl Aldehyde and Its N-Sulfonylimine via Rh Catalysis journal August 2012
Direct Access to Acylated Azobenzenes via Pd-Catalyzed C–H Functionalization and Further Transformation into an Indazole Backbone journal January 2013
Direct transition metal-catalyzed functionalization of heteroaromatic compounds journal January 2007
A general and efficient approach to 2H-indazoles and 1H-pyrazoles through copper-catalyzed intramolecular N–N bond formation under mild conditions journal January 2011
Rhodium(iii)-catalyzed oxidative carbonylation of benzamides with carbon monoxide journal January 2011
Azobenzene photoswitches for biomolecules journal January 2011
Towards mild metal-catalyzed C–H bond activation journal January 2011
Rhodium-catalyzed oxidative C2-acylation of indoles with aryl and alkyl aldehydes journal January 2012
C–C, C–O and C–N bond formation via rhodium(iii)-catalyzed oxidative C–H activation journal January 2012
Mechanistic understanding of Rh-catalyzed N-sulfonylaldimine insertion into aryl C–H bonds journal January 2012
Rhodium(iii)-catalyzed synthesis of phthalides by cascade addition and cyclization of benzimidates with aldehydes journal January 2012
Rapid and general profiling of protease specificity by using combinatorial fluorogenic substrate libraries journal June 2000
Biotinylated Rh(III) Complexes in Engineered Streptavidin for Accelerated Asymmetric C-H Activation journal October 2012
Chiral Cyclopentadienyl Ligands as Stereocontrolling Element in Asymmetric C–H Functionalization journal October 2012
The Davis-Beirut Reaction: A Novel Entry into 2H-indazoles and Indazolones. Recent Biological Activity of Indazoles journal September 2012

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