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Visible Light-Promoted Friedel–Crafts-Type Chloroacylation of Alkenes to β-Chloroketones
Organic Letters ( IF 4.9 ) Pub Date : 2020-03-27 , DOI: 10.1021/acs.orglett.0c00788 Dilip V. Patil 1 , Hun Young Kim 1 , Kyungsoo Oh 1
Organic Letters ( IF 4.9 ) Pub Date : 2020-03-27 , DOI: 10.1021/acs.orglett.0c00788 Dilip V. Patil 1 , Hun Young Kim 1 , Kyungsoo Oh 1
Affiliation
The photoredox chloroacylation of alkenes has been developed as a substitute for the Friedel–Crafts acylation of alkenes to β-chloroketones. The direct generation of acyl radical species from acid chlorides under the photoredox conditions allows the formation of β-chloroketones without dehydrochlorination with the help of KHCO3. The synthetic utility of the current method is demonstrated in the one-pot synthesis of dihydroisoxazole, dihydropyrazole, and dihydropyrimidine-2-thione in 1 mmol scale.
中文翻译:
可见光促进烯烃的Friedel-Crafts型氯酰化为β-氯酮
烯烃的光氧化还原氯酰化已被开发出来,可以替代烯烃的Friedel-Crafts酰化为β-氯酮。在光氧化还原条件下,由酰氯直接生成酰基自由基种类,无需借助KHCO 3进行脱氯化氢即可形成β-氯酮。当前方法的合成效用已在1毫摩尔规模的一锅合成二氢异恶唑,二氢吡唑和二氢嘧啶-2-硫酮中得到了证明。
更新日期:2020-04-24
中文翻译:
可见光促进烯烃的Friedel-Crafts型氯酰化为β-氯酮
烯烃的光氧化还原氯酰化已被开发出来,可以替代烯烃的Friedel-Crafts酰化为β-氯酮。在光氧化还原条件下,由酰氯直接生成酰基自由基种类,无需借助KHCO 3进行脱氯化氢即可形成β-氯酮。当前方法的合成效用已在1毫摩尔规模的一锅合成二氢异恶唑,二氢吡唑和二氢嘧啶-2-硫酮中得到了证明。