铜催化的烷基硼酸酯的立体特异性转化。
Copper-Catalyzed Stereospecific Transformations of Alkylboronic Esters.
机构信息
Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, United States.
出版信息
J Am Chem Soc. 2022 Jul 6;144(26):11546-11552. doi: 10.1021/jacs.2c04037. Epub 2022 Jun 23.
Abstract
Copper-catalyzed stereospecific cross-couplings of boronic esters are reported. Boron "ate" complexes derived from pinacol boronic esters and -butyl lithium undergo stereospecific transmetalation to copper cyanide, followed by coupling with alkynyl bromides, allyl halides, propargylic halides, β-haloenones, hydroxylamine esters, and acyl chlorides. Through this simple transformation, commercially available inexpensive compounds can be employed to convert primary and secondary alkylboronic esters to a wide array of synthetically useful compounds.
摘要
报道了硼酸酯的铜催化立体特异性交叉偶联反应。频哪醇硼酸酯与正丁基锂衍生的硼“ate”配合物经历立体特异性的transmetallation 到氰化亚铜，随后与炔基溴化物、烯丙基卤化物、丙炔基卤化物、β-卤代烯酮、羟胺酯和酰氯进行偶联。通过这种简单的转化，可以利用商业可得的廉价化合物将伯和仲烷基硼酸酯转化为广泛的合成有用的化合物。
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