Sureshbabu Popuri, Azeez Sadaf, Muniyappan Nalluchamy, Sabiah Shahulhameed, Kandasamy Jeyakumar
Department of Chemistry , Indian Institute of Technology (BHU) , Varanasi , Uttar Pradesh 221005 , India.
Department of Chemistry , Pondicherry University , Pondicherry 605014 , India.
J Org Chem. 2019 Sep 20;84(18):11823-11838. doi: 10.1021/acs.joc.9b01699. Epub 2019 Sep 4.
Conversion of a wide range of -Boc amides to aryl ketones was achieved with Grignard reagents via chemoselective C(O)-N bond cleavage. The reactions proceeded under catalyst-free conditions with different aryl, alkyl, and alkynyl Grignard reagents. α-Ketoamide was successfully converted to aryl diketones, while α,β-unsaturated amide underwent 1,4-addition followed by C(O)-N bond cleavage to provide diaryl propiophenones. -Boc amides displayed higher reactivity than Weinreb amides with Grignard reagents. A broad substrate scope, excellent yields, and quick conversion are important features of this methodology.
通过化学选择性C（O）-N键裂解，使用格氏试剂实现了多种-Boc酰胺向芳基酮的转化。反应在无催化剂条件下，与不同的芳基、烷基和炔基格氏试剂进行。α-酮酰胺成功转化为芳基二酮，而α，β-不饱和酰胺则先进行1,4-加成，然后进行C（O）-N键裂解，得到二芳基苯丙酮。-Boc酰胺与格氏试剂反应时比Weinreb酰胺表现出更高的反应活性。底物范围广、产率高和转化迅速是该方法的重要特点。
