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Ligand-Controlled Direct γ-C-H Arylation of Aldehydes.
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2020-01-21 , DOI: 10.1002/anie.201913126 Bijin Li 1 , Brianna Lawrence 1 , Guigen Li 2, 3 , Haibo Ge 1
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2020-01-21 , DOI: 10.1002/anie.201913126 Bijin Li 1 , Brianna Lawrence 1 , Guigen Li 2, 3 , Haibo Ge 1
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The first example of PdII -catalyzed γ-C(sp3 )-H functionalization of aliphatic and benzoheteroaryl aldehydes has been developed using a transient ligand and an external ligand, concurrently. A wide array of γ-arylated aldehydes were readily accessed without preinstalling internal directing groups. The catalytic mechanism was studied by performing deuterium-labelling experiments, which indicated that the γ-C(sp3 )-H bond cleavage is the rate-limiting step during the reaction process. This reaction could be performed on a gram scale, and also demonstrated its potential application in the synthesis of new mechanofluorochromic materials with blue-shifted mechanochromic properties.
中文翻译：
配体控制的直接γ-CH醛化。
同时使用瞬态配体和外部配体开发了PdII催化的脂肪族和苯并杂芳基醛的γ-C（sp3）-H官能化的第一个例子。无需预先安装内部导向基团即可轻松获得各种各样的γ-芳基化醛。通过氘标记实验研究了其催化机理，表明γ-C（sp3）-H键的裂解是反应过程中的限速步骤。该反应可以以克为单位进行，并且还证明了其在具有蓝移的机械变色特性的新的机械荧光变色材料的合成中的潜在应用。
更新日期：2020-01-22
中文翻译：
配体控制的直接γ-CH醛化。
同时使用瞬态配体和外部配体开发了PdII催化的脂肪族和苯并杂芳基醛的γ-C（sp3）-H官能化的第一个例子。无需预先安装内部导向基团即可轻松获得各种各样的γ-芳基化醛。通过氘标记实验研究了其催化机理，表明γ-C（sp3）-H键的裂解是反应过程中的限速步骤。该反应可以以克为单位进行，并且还证明了其在具有蓝移的机械变色特性的新的机械荧光变色材料的合成中的潜在应用。
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