螺旋桨烷
化学
卤素
苯氮卓类
组合化学
烷基
磺酰
双环分子
试剂
环丁烷
卤化物
有机化学
环加成
催化作用
作者
Helena D. Pickford,Vasyl Ripenko,Ryan E. McNamee,Serhii Holovchuk,Amber L. Thompson,Russell C. Smith,Pavel K. Mykhailiuk,Edward A. Anderson
标识
DOI:10.1002/anie.202213508
摘要
Sulfonylated aromatics are commonplace motifs in drugs and agrochemicals. However, methods for the direct synthesis of sulfonylated non-classical arene bioisosteres, which could improve the physicochemical properties of drug and agrochemical candidates, are limited. Here we report a solution to this challenge: a one-pot halosulfonylation of [1.1.1]propellane, [3.1.1]propellane and bicyclo[1.1.0]butanes that proceeds under practical, scalable and mild conditions. The sulfonyl halides used in this chemistry feature aryl, heteroaryl and alkyl substituents, and are conveniently generated in situ from readily available sulfinate salts and halogen atom sources. This methodology enables the synthesis of an array of pharmaceutically and agrochemically relevant halogen/sulfonyl-substituted bioisosteres and cyclobutanes, on up to multidecagram scale.
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