磺酰
电泳剂
金属转移
化学
反应性(心理学)
芳基
组合化学
催化作用
铃木反应
药物化学
有机化学
钯
医学
病理
替代医学
烷基
作者
Paul Chatelain,Cyprien Muller,Abhijit Sau,Daria Brykczyńska,Maryam Bahadori,Christopher N. Rowley,Joseph Moran
标识
DOI:10.1002/anie.202111977
摘要
Sulfonyl fluorides have emerged as powerful "click" electrophiles to access sulfonylated derivatives. Yet, they are relatively inert towards C-C bond forming transformations, notably under transition-metal catalysis. Here, we describe conditions under which aryl sulfonyl fluorides act as electrophiles for the Pd-catalyzed Suzuki-Miyaura cross-coupling. This desulfonative cross-coupling occurs selectively in the absence of base and, unusually, even in the presence of strong acids. Divergent one-step syntheses of two analogues of bioactive compounds showcase the expanded reactivity of sulfonyl fluorides to encompass both S-Nu and C-C bond formation. Mechanistic experiments and DFT calculations suggest oxidative addition occurs at the C-S bond followed by desulfonation to form a Pd-F intermediate that facilitates transmetalation.
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