title: The Synthesis of Alkyl and (Hetero)aryl Sulfonamides From Sulfamoyl Inner Salts.
abstract: An approach to the synthesis of sulfonamides from sulfamoyl inner salts and organometallic species is presented. A range of sulfamoyl carbamates, amines, and metals are explored. Primary, secondary, and tertiary alkyl-, aryl-, and heteroaryllitihium and magnesium nucleophiles were successful. This approach yields bench-stable intermediates and avoids many of the functional group incompatibilities, regioselectivity issues, and high-energy reagents generally associated with the synthesis of sulfonamides. Additionally, the products may be purified by basic extraction or salt formation, avoiding chromatography.
authors.affiliation: Worldwide Medicinal Chemistry, Pfizer Worldwide Research and Development, Eastern Point Road, Groton, Connecticut 06340, United States.
authors.forename: Joseph M
authors.initials: JM
authors.lastname: Young
authors.affiliation: Worldwide Medicinal Chemistry, Pfizer Worldwide Research and Development, Eastern Point Road, Groton, Connecticut 06340, United States.
authors.forename: Aisha G
authors.initials: AG
authors.lastname: Lee
authors.affiliation: Worldwide Medicinal Chemistry, Pfizer Worldwide Research and Development, Eastern Point Road, Groton, Connecticut 06340, United States.
authors.forename: Ramalakshmi Y
authors.initials: RY
authors.lastname: Chandrasekaran
authors.affiliation: Worldwide Medicinal Chemistry, Pfizer Worldwide Research and Development, Eastern Point Road, Groton, Connecticut 06340, United States.
authors.forename: Joseph W
authors.initials: JW
authors.lastname: Tucker
mesh_terms: D002219:Carbamates / Q000737:chemistry*; D002384:Catalysis; D007202:Indicators and Reagents / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D002219:Carbamates; D007202:Indicators and Reagents; D009942:Organometallic Compounds; D013449:Sulfonamides