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Coupling Reaction between Aldehydes and Non-Activated Hydrocarbons via the Reductive Radical-Polar Crossover Pathway.
Organic Letters ( IF 4.9 ) Pub Date : 2020-01-15 , DOI: 10.1021/acs.orglett.0c00096
Kenzo Yahata 1 , Shu Sakurai 1 , Shuhei Hori 1 , Shin Yoshioka 1 , Yuki Kaneko 1 , Kai Hasegawa 1 , Shuji Akai 1
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Herein, we describe the generation of an organochromium-type carbanion species from a non-activated C-H bond and its nucleophilic addition to aldehydes. The catalytic carbanion generation occurred through formal deprotonation of a non-activated C-H bond under mild conditions and did not need the prefunctionalization or anion stabilizing group. Carbon radical intermediates generated by decatungstate photocatalyst-mediated hydrogen abstraction were captured by a chromium salt with the reductive radical-polar crossover reaction to produce organochromium carbanions.

中文翻译:

醛与非活性碳氢化合物之间通过还原性自由基-极性交换途径的偶联反应。

在本文中,我们描述了由未活化的CH键生成有机铬型碳负离子及其对醛的亲核加成反应。催化碳负离子的产生通过温和条件下未活化的CH键的正式去质子化而发生,不需要预官能化或阴离子稳定基团。铬酸盐通过还原自由基-极性交叉反应捕获由去阳离子钨酸盐光催化剂介导的氢提取产生的碳自由基中间体,从而生成有机铬碳负离子。
更新日期:2020-01-15
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