Synthesis of fluorinated allylic alcohols via photoinduced decarboxylative cross-coupling of α-fluoroacrylic acids and alcohols†

Xiao-Yu Lu , Meng-Ting Gao , Li-Juan Yu , Hong-Ye Pan , Xiang Zhang , Rui Huang , Kang Yang , Fu-Yi Shui , Yi-Wei Song , Gui-Xian Yang
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Abstract

Herein, a practical and robust methodology for photoinduced decarboxylative and dehydrogenative cross-coupling is reported. A wide range of α-fluoroacrylic acids and structurally diverse alcohols were smoothly converted into the desired fluorinated allylic alcohols with high Z-stereoselectivity under mild conditions. These fluorinated allylic alcohols are versatile building blocks and important structural fragments in organic chemistry and pharmaceutical science. The feasibility of this synthetic strategy was fully demonstrated via a gram-scale reaction, further transformations, and late-stage modifications of bioactive molecules.

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通过α-氟丙烯酸和醇的光诱导脱羧交叉偶联合成氟化烯丙醇†
本文报道了一种实用而稳健的光诱导脱羧和脱氢交叉偶联方法。在温和的条件下,广泛的α-氟丙烯酸和结构多样的醇被顺利地转化为所需的具有高Z-立体选择性的氟化烯丙醇。这些氟化烯丙醇是有机化学和药物科学中的多功能构建块和重要结构片段。通过克级反应、进一步转化和生物活性分子的后期修饰,充分证明了这种合成策略的可行性。
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Synthesis of biologically active [1,5]diazocino[2,1-b]quinazolinones through [4 + 4] cycloaddition of 2-alkynyl quinazolinones with aza-ortho-quinone methides† Synthesis of fluorinated allylic alcohols via photoinduced decarboxylative cross-coupling of α-fluoroacrylic acids and alcohols† Aromatization-driven cascade [1,5]-hydride transfer/cyclization for synthesis of spirochromanes† Playing with the cavity size of exTTF-based self-assembled cages† An alternative approach to triazatruxene synthesis and derivatization to a boron difluoride complex†
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