Nucleophilic Ortho Allylation of Aryl and Heteroaryl Sulfoxides
Nucleophilic Ortho Allylation of Aryl and Heteroaryl Sulfoxides
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DOI：
10.1021/ol2025197
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发表时间：
2011-11-04
期刊：
影响因子：
5.2
通讯作者：
Procter, David J.
中科院分区：
文献类型：
--
作者：
Eberhart, Andrew J.;Imbriglio, Jason E.;Procter, David J.
芳基和杂芳基亚砜在用Tf 2 O和烯丙基硅烷处理时进行邻位烯丙基化。该方法补充了亚砜的使用，以指导邻位金属化和与亲电试剂的反应，因为它允许烯丙基碳亲核试剂在无金属过程中被添加到定向基团的邻位。通用的硫化物加合物可以使用各种方法选择性地操作，包括有机硫基基团的Kumada-Corriu交叉偶联。
Aryl and heteroaryl sulf oxides undergo ortho allylation upon treatment with Tf2O and allyisilanes. The method complements the use of sulfoxides to direct ortho-metalation and reaction with electrophiles as it allows allylic carbon nucleophiles to be added ortho to the directing group in a metal-free process. The versatile sulfide adducts can be selectively manipulated using various methods Including Kumada-Corriu cross-coupling of the organosulfanyl group.