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Synthesis of Alkyl and Aryl Boronate Esters via CeO2-Catalyzed Borylation of Alkyl and Aryl Electrophiles Including Alkyl Chlorides
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2023-11-13 , DOI: 10.1021/acs.joc.3c01755 Ramesh Bhawar 1 , Suresh Saini 1 , Kiran S Patil 1 , D H Nagaraju 2 , Shubhankar Kumar Bose 1
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2023-11-13 , DOI: 10.1021/acs.joc.3c01755 Ramesh Bhawar 1 , Suresh Saini 1 , Kiran S Patil 1 , D H Nagaraju 2 , Shubhankar Kumar Bose 1
Affiliation
A recyclable protocol using a CeO2-nanorod catalyst for borylation of alkyl halides with B2pin2 (pin = OCMe2CMe2O) is reported. A wide range of synthetically useful alkyl boronate esters are readily obtained from primary and secondary alkyl electrophiles, including unactivated alkyl chlorides, demonstrating broad utility and functional group tolerance. Preliminary investigation revealed an involvement of in situ formed catalytically active boryl species. The catalyst can be reused for up to six runs without appreciable loss in activity. In addition, we have demonstrated the use of this recyclable catalyst for the borylation of aryl halides with B2pin2, providing valuable aryl boronate esters under neat conditions.
中文翻译:
通过 CeO2 催化烷基和芳基亲电子试剂(包括烷基氯)硼化合成烷基和芳基硼酸酯
报道了使用CeO 2 -纳米棒催化剂用B 2 pin 2 (pin = OCMe 2 CMe 2 O)对卤代烷进行硼基化的可回收方案。多种合成上有用的烷基硼酸酯很容易从伯烷基和仲烷基亲电子试剂(包括未活化的烷基氯)获得,表现出广泛的用途和官能团耐受性。初步调查显示,其中涉及原位形成的催化活性硼基物质。该催化剂可重复使用最多六次,而不会明显降低活性。此外,我们还展示了这种可回收催化剂用于芳基卤化物与 B 2 pin 2的硼基化,在纯净条件下提供有价值的芳基硼酸酯。
更新日期:2023-11-13
中文翻译:
通过 CeO2 催化烷基和芳基亲电子试剂(包括烷基氯)硼化合成烷基和芳基硼酸酯
报道了使用CeO 2 -纳米棒催化剂用B 2 pin 2 (pin = OCMe 2 CMe 2 O)对卤代烷进行硼基化的可回收方案。多种合成上有用的烷基硼酸酯很容易从伯烷基和仲烷基亲电子试剂(包括未活化的烷基氯)获得,表现出广泛的用途和官能团耐受性。初步调查显示,其中涉及原位形成的催化活性硼基物质。该催化剂可重复使用最多六次,而不会明显降低活性。此外,我们还展示了这种可回收催化剂用于芳基卤化物与 B 2 pin 2的硼基化,在纯净条件下提供有价值的芳基硼酸酯。