C-halogen bond formation

Groves, John T.; Liu, Wei

C-halogen bond formation

Patent · Tue Feb 05 04:00:00 EST 2019

OSTI ID:1502471

Groves, John T.; Liu, Wei

Methods of halogenating a carbon containing compound having an sp3 C--H bond are provided. Methods of fluorinating a carbon containing compound comprising halogenation with Cl or Br followed by nucleophilic substitution with F are provided. Methods of direct oxidative C--H fluorination of a carbon containing compound having an sp3 C--H bond are provided. The halogenated products of the methods are provided.

View Patent

Research Organization:: Princeton Univ., Princeton, NJ (United States)

Sponsoring Organization:: USDOE

DOE Contract Number:: SC0001298

Assignee:: The Trustees Of Princeton University (Princeton, NJ)

Patent Number(s):: 10,196,341

Application Number:: 14/239,706

OSTI ID:: 1502471

Country of Publication:: United States

Language:: English

References (22)

Unprecedented Rate Enhancements of Hydrogen-Atom Transfer to a Manganese(V)-Oxo Corrolazine Complex Prokop, Katharine A.; de Visser, Sam P.; Goldberg, David P. Angewandte Chemie International Edition, Vol. 49, Issue 30 https://doi.org/10.1002/anie.201001172	journal	June 2010
Polystyrene-bound 1,4-phenylenediamine as a heterogeneous axial ligand for Mn(salophen)Cl and its use as biomimetic alkene epoxidation and alkane hydroxylation catalyst with sodium periodate Mirkhani, Valiollah; Moghadam, Majid; Tangestaninejad, Shahram Polyhedron, Vol. 25, Issue 15 https://doi.org/10.1016/j.poly.2006.04.020	journal	November 2006
Synergetic combination of catalysis of the phase transfer-electron transfer type for the oxidation of alcohols or hydrocarbons Tabushi, Iwao; Koga, Noboru Tetrahedron Letters, Vol. 20, Issue 38 https://doi.org/10.1016/S0040-4039(01)95496-6	journal	January 1979
Trigonal-Bipyramidal Geometry Induced by an External Water Ligand in a Sterically Hindered Iron Salen Complex, Related to the Active Site of Protocatechuate 3,4-Dioxygenase Kurahashi, Takuya; Oda, Kenji; Sugimoto, Manabu Inorganic Chemistry, Vol. 45, Issue 19 https://doi.org/10.1021/ic060650p	journal	September 2006
Selective electrolytic fluorinations in 70% HF/30% pyridine Lee, Sarah M.; Roseman, Jamie M.; Blair Zartman, C. Journal of Fluorine Chemistry, Vol. 77, Issue 1 https://doi.org/10.1016/0022-1139(95)03379-3	journal	March 1996
Alkane activation and functionalization under mild conditions by a homogeneous manganese(III)porphyrin-iodosylbenzene oxidizing system Hill, Craig L.; Schardt, Bruce C. Journal of the American Chemical Society, Vol. 102, Issue 20 https://doi.org/10.1021/ja00540a049	journal	September 1980
Catalytic replacement of unactivated alkane carbon-hydrogen bonds with carbon-X bonds (X = nitrogen, oxygen, chlorine, bromine, or iodine). Coupling of intermolecular hydrocarbon activation by MnIIITPPX complexes with phase-transfer catalysis Hill, Craig L.; Smegal, John A.; Henly, Timothy J. The Journal of Organic Chemistry, Vol. 48, Issue 19 https://doi.org/10.1021/jo00167a023	journal	September 1983
Catalytic homogeneous functionalization of adamantane. Influence of electronic and structural features of the metalloporphyrin catalyst on atom transfer selectivity (oxygenation versus acidification/halogenation) Brown, Robert B.; Hill, Craig L. The Journal of Organic Chemistry, Vol. 53, Issue 24 https://doi.org/10.1021/jo00259a028	journal	November 1988
Silver-Catalyzed Late-Stage Fluorination Tang, Pingping; Furuya, Takeru; Ritter, Tobias Journal of the American Chemical Society, Vol. 132, Issue 34 https://doi.org/10.1021/ja105834t	journal	September 2010
Manganese Catalyzed C–H Halogenation Liu, Wei; Groves, John T. Accounts of Chemical Research, Vol. 48, Issue 6 https://doi.org/10.1021/acs.accounts.5b00062	journal	May 2015
Mechanochemical unzipping of insulating polyladderene to semiconducting polyacetylene Chen, Zhixing; Mercer, Jaron A. M.; Zhu, Xiaolei Science, Vol. 357, Issue 6350 https://doi.org/10.1126/science.aan2797	journal	August 2017
A DBFOX-Ph-Based Combinatorial Catalyst for Enantioselective Fluorination of Aryl Acetyl and 3-Butenoyl Thiazolidinones Reddy, Dhande Sudhakar; Shibata, Norio; Horikawa, Takao Chemistry - An Asian Journal, Vol. 4, Issue 9 https://doi.org/10.1002/asia.200900164	journal	September 2009
Catalytic hydroxylation of saturated hydrocarbons with the sodium hypohalite/manganese porphyrin system De Poorter, Bertha; Ricci, Marco; Bortolini, Olga Journal of Molecular Catalysis, Vol. 31, Issue 2 https://doi.org/10.1016/0304-5102(85)85065-3	journal	July 1985
Critical Role of External Axial Ligands in Chirality Amplification of trans -Cyclohexane-1,2-diamine in Salen Complexes Kurahashi, Takuya; Hada, Masahiko; Fujii, Hiroshi Journal of the American Chemical Society, Vol. 131, Issue 34 https://doi.org/10.1021/ja904635n	journal	September 2009
Mechanism of Oxidation Reactions Catalyzed by Cytochrome P450 Enzymes Meunier, Bernard; de Visser, Samuël P.; Shaik, Sason Chemical Reviews, Vol. 104, Issue 9 https://doi.org/10.1021/cr020443g	journal	September 2004
Nickel(salen) catalysed chlorination of saturated hydrocarbons by sodium hypochlorite Querci, Cecilia; Strologo, Sauro; Ricci, Marco Tetrahedron Letters, Vol. 31, Issue 45 https://doi.org/10.1016/S0040-4039(00)97121-1	journal	January 1990
Radical Autoxidation and Autogenous O ₂ Evolution in Manganese−Porphyrin Catalyzed Alkane Oxidations with Chlorite Slaughter, LeGrande M.; Collman, James P.; Eberspacher, Todd A. Inorganic Chemistry, Vol. 43, Issue 17 https://doi.org/10.1021/ic049922j	journal	August 2004
A Practical and Convenient Fluorination of 1,3-Dicarbonyl Compounds Using Aqueous HF in the Presence of Iodosylbenzene Kitamura, Tsugio; Kuriki, Satoshi; Morshed, Mohammad Hasan Organic Letters, Vol. 13, Issue 9 https://doi.org/10.1021/ol200632d	journal	May 2011
Enantioselective Organocatalytic α-Fluorination of Aldehydes Beeson, Teresa D.; MacMillan, David W. C. Journal of the American Chemical Society, Vol. 127, Issue 24 https://doi.org/10.1021/ja051805f	journal	June 2005
Manganese-Catalyzed Oxidative Benzylic C-H Fluorination by Fluoride Ions Liu, Wei; Groves, John T. Angewandte Chemie International Edition, Vol. 52, Issue 23 https://doi.org/10.1002/anie.201301097	journal	April 2013
Manganese Porphyrins Catalyze Selective C−H Bond Halogenations Liu, Wei; Groves, John T. Journal of the American Chemical Society, Vol. 132, Issue 37 https://doi.org/10.1021/ja105548x	journal	September 2010
Darstellung von primaren alkylfluoriden unter einsatz der phasen transfer katalyse Dermiek, Salman; Sasson, Yoel Journal of Fluorine Chemistry, Vol. 22, Issue 5 https://doi.org/10.1016/S0022-1139(00)81165-3	journal	May 1983

Similar Records

Pyrrolo isoquinolines

Patent · Fri Dec 31 23:00:00 EST 1999 · OSTI ID:873450

Polymerization catalyst, production and use

Patent · Mon Jan 05 23:00:00 EST 1987 · OSTI ID:7122058

Low equivalent weight polymers

Patent · Tue Jul 18 00:00:00 EDT 2017 · OSTI ID:1532003

C-halogen bond formation

Citation Formats

References (22)

Similar Records

Related Subjects