Abstract
We report the synthesis of sulfinamides using organometallic reagents, a sulfur dioxide reagent, and nitrogen based-nucleophiles. The addition of an organometallic reagent to the commercially available sulfur dioxide surrogate, DABSO, generates a metal sulfinate which is reacted with thionyl chloride to form a sulfinyl chloride intermediate. Trapping the sulfinyl chlorides in situ with a variety of nitrogen nucleophiles delivers sulfinamides in 32–83% yields. Each stage of the process is performed at room temperature, and the total reaction time is only 1.5 h.
Highlights
Sulfinamides are a broadly useful class of functional groups in organic chemistry
Racemic sulfinamides are usually prepared from sulfinic acids or sulfinate salts, most commonly by reaction with oxalyl chloride[6] or thionyl chloride6e,7 to give sulfinyl chloride intermediates which react with amines (Scheme 1a), or by direct coupling with amines using DCC8 or EDCI.[9]
Prior work had shown that a range of sulfinyl chlorides, including heteroaryl sulfinyl chlorides, had shown promising reactivity with nitrogen-based nucleophiles,6e and as such, our approach was based on reacting in situ formed metal sulfinates with either thionyl chloride or oxalyl chloride to prepare sulfinyl chloride intermediates
Summary
Sulfinamides are a broadly useful class of functional groups in organic chemistry. Chiral sulfinamides have been widely used as chiral auxiliaries,[1] as ligands in transition-metal catalysis,[2] and as organocatalysts.[3].
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