BIOMAT Database Logo BIOMAT Database Logo

Synthesis of sulfones from organozinc reagents, DABSO, and alkyl halides. 2014

Benjamin N Rocke, and Kevin B Bahnck, and Michael Herr, and Sophie Lavergne, and Vincent Mascitti, and Christian Perreault, and Jana Polivkova, and Andrei Shavnya
Pfizer Worldwide Medicinal Chemistry , Eastern Point Road, Groton, Connecticut 06340, United States.

Organozinc reagents react with the SO2 surrogate DABSO, and the resulting zinc sulfinate salts are alkylated in situ to afford sulfones. This transformation has a broad scope and is compatible with a wide range of structural motifs of medicinal chemistry relevance including nitrile, secondary carbamates, and nitrogen-containing heterocycles.

UI MeSH Term Description Entries
D009942 Organometallic Compounds A class of compounds of the type R-M, where a C atom is joined directly to any other element except H, C, N, O, F, Cl, Br, I, or At. (Grant & Hackh's Chemical Dictionary, 5th ed) Metallo-Organic Compound,Metallo-Organic Compounds,Metalloorganic Compound,Organometallic Compound,Metalloorganic Compounds,Compound, Metallo-Organic,Compound, Metalloorganic,Compound, Organometallic,Compounds, Metallo-Organic,Compounds, Metalloorganic,Compounds, Organometallic,Metallo Organic Compound,Metallo Organic Compounds
D003622 Dapsone A sulfone active against a wide range of bacteria but mainly employed for its actions against MYCOBACTERIUM LEPRAE. Its mechanism of action is probably similar to that of the SULFONAMIDES which involves inhibition of folic acid synthesis in susceptible organisms. It is also used with PYRIMETHAMINE in the treatment of malaria. (From Martindale, The Extra Pharmacopoeia, 30th ed, p157-8) Diaminodiphenylsulfone,Sulfonyldianiline,4,4'-Diaminophenyl Sulfone,Avlosulfone,DADPS,Dapsoderm-X,Dapson-Fatol,Diaphenylsulfone,Disulone,Sulfona,4,4' Diaminophenyl Sulfone,Sulfone, 4,4'-Diaminophenyl
D006846 Hydrocarbons, Halogenated Hydrocarbon compounds with one or more HYDROGEN atoms substituted with HALOGENS. Halogenated Hydrocarbons
D013450 Sulfones Sulfone
D015032 Zinc A metallic element of atomic number 30 and atomic weight 65.38. It is a necessary trace element in the diet, forming an essential part of many enzymes, and playing an important role in protein synthesis and in cell division. Zinc deficiency is associated with ANEMIA, short stature, HYPOGONADISM, impaired WOUND HEALING, and geophagia. It is known by the symbol Zn.
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular

Related Publications

Benjamin N Rocke, and Kevin B Bahnck, and Michael Herr, and Sophie Lavergne, and Vincent Mascitti, and Christian Perreault, and Jana Polivkova, and Andrei Shavnya
Photoredox Activation of Organozinc Reagents: Barbier-Type Reaction of Alkyl Halides with α-(Trifluoromethyl)styrenes.
December 2021, Organic letters,
Benjamin N Rocke, and Kevin B Bahnck, and Michael Herr, and Sophie Lavergne, and Vincent Mascitti, and Christian Perreault, and Jana Polivkova, and Andrei Shavnya
CuI catalyzed sulfonylation of organozinc reagents with sulfonyl halides.
July 2014, Organic & biomolecular chemistry,
Benjamin N Rocke, and Kevin B Bahnck, and Michael Herr, and Sophie Lavergne, and Vincent Mascitti, and Christian Perreault, and Jana Polivkova, and Andrei Shavnya
Palladium-Catalyzed Synthesis of (Hetero)Aryl Alkyl Sulfones from (Hetero)Aryl Boronic Acids, Unactivated Alkyl Halides, and Potassium Metabisulfite.
November 2015, Angewandte Chemie (International ed. in English),
Benjamin N Rocke, and Kevin B Bahnck, and Michael Herr, and Sophie Lavergne, and Vincent Mascitti, and Christian Perreault, and Jana Polivkova, and Andrei Shavnya
Nickel-catalyzed cross-coupling reaction of alkyl halides with organozinc and Grignard reagents with 1,3,8,10-tetraenes as additives.
November 2004, Angewandte Chemie (International ed. in English),
Benjamin N Rocke, and Kevin B Bahnck, and Michael Herr, and Sophie Lavergne, and Vincent Mascitti, and Christian Perreault, and Jana Polivkova, and Andrei Shavnya
Sulfinamide Synthesis Using Organometallic Reagents, DABSO, and Amines.
May 2020, The Journal of organic chemistry,
Benjamin N Rocke, and Kevin B Bahnck, and Michael Herr, and Sophie Lavergne, and Vincent Mascitti, and Christian Perreault, and Jana Polivkova, and Andrei Shavnya
Organozinc generation via the titanium-catalyzed activation of alkyl halides.
December 2009, Organic letters,
Benjamin N Rocke, and Kevin B Bahnck, and Michael Herr, and Sophie Lavergne, and Vincent Mascitti, and Christian Perreault, and Jana Polivkova, and Andrei Shavnya
Synthesis of alkyl and aryl C-pyranosides using organozinc reagents via a Ferrier-type rearrangement.
February 2005, Carbohydrate research,
Benjamin N Rocke, and Kevin B Bahnck, and Michael Herr, and Sophie Lavergne, and Vincent Mascitti, and Christian Perreault, and Jana Polivkova, and Andrei Shavnya
Fischer indole synthesis with organozinc reagents.
December 2010, Angewandte Chemie (International ed. in English),
Benjamin N Rocke, and Kevin B Bahnck, and Michael Herr, and Sophie Lavergne, and Vincent Mascitti, and Christian Perreault, and Jana Polivkova, and Andrei Shavnya
Enantioselective Radical Addition/Cross-Coupling of Organozinc Reagents, Alkyl Iodides, and Alkenyl Boron Reagents.
October 2019, Angewandte Chemie (International ed. in English),
Benjamin N Rocke, and Kevin B Bahnck, and Michael Herr, and Sophie Lavergne, and Vincent Mascitti, and Christian Perreault, and Jana Polivkova, and Andrei Shavnya
Synthesis of Heteroaryl Sulfonamides from Organozinc Reagents and 2,4,6-Trichlorophenyl Chlorosulfate.
June 2015, Organic letters,
Copied contents to your clipboard!