Copper-catalyzed fragmentation-rearrangement sequence of cycloketoxime esters

被引：3
|
作者：
Wu, Yixiao [1 ]
Zhao, Binlin [2 ]
Shi, Zhuangzhi [3 ]
Yuan, Yu [1 ]
机构：
[1] Yangzhou Univ, Coll Chem & Chem Engn, Yangzhou 225002, Jiangsu, Peoples R China
[2] Nanjing Forestry Univ, Coll Sci, Nanjing 210037, Peoples R China
[3] Nanjing Univ, Sch Chem & Chem Engn, State Key Lab Coordinat Chem, Nanjing 210093, Peoples R China
来源：
TETRAHEDRON | 2020年 / 76卷 / 05期
关键词：
Copper; Radical; Cycloketoxime esters; C-C bond cleavage; Fragmentation-rearrangement; C-C BOND; CARBON-CARBON BONDS; CYCLOBUTANONE OXIME ESTERS; IMINYL RADICALS; RING-CLEAVAGE; TERT-CYCLOBUTANOLS; H CYANOALKYLATION; ACYL OXIMES; ACTIVATION; ALKENES;
D O I：
10.1016/j.tet.2019.130873
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Copper-catalyzed fragmentation-rearrangement sequence of cycloketoxime esters is reported. This strategy provides direct access to diverse ring-opening acyloxylation nitriles avoiding the use of toxic cyanic reagents with good atom economy and well functional group tolerance. Experimental exploration showed that tetrabutylammonium bromide (TBAB) played an irreplaceable role in this transformation. Based on the primary mechanistic experiments, a plausible mechanism was also proposed. (C) 2019 Elsevier Ltd. All rights reserved.
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页数：7
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