Metal-Free Direct Alkylation of Ketene Dithioacetals by Oxidative C(sp~2)-H/C(sp~3)-H Cross-Coupling

Jiangwei Wen; Fan Zhang; Wenyan Shi; Aiwen Lei

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Metal-Free Direct Alkylation of Ketene Dithioacetals by Oxidative C(sp~2)-H/C(sp~3)-H Cross-Coupling

机译：通过氧化C（SP〜2）-H / C（SP〜3）-H交叉耦合的无金属直接烷基化酮二缩醛

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The functionalization of internal olefins has been a challenging task in organic synthesis. This protocol provides an efficient and transition-metal-free direct oxidative C(sp_2)-H/C(sp_3)-H cross-coupling method to access tetrasubstituted olefins. The push-pull effect from the polarized olefin substrates accelerates the internal olefin C- H alkylation. Importantly, the mechanistic experimental results demonstrate that the alkanes C-H bond cleavage is the rate-determining step, and a radical pathway has been proposed for the alkylation reaction. Notably, the present protocol has excellent functional group tolerance and could be easily scaled up with good efficiency.

机译：内烯烃的官能化在有机合成中是一个具有挑战性的任务。该方案提供了一种有效且过渡 - 无金属直接氧化C（SP_2）-H / C（SP_3）-H交叉偶联方法，以进入四氢烯烃。来自偏振烯烃基材的推挽效果加速了内烯烃C-H烷基化。重要的是，机械实验结果表明，烷烃C-H键切割是速率确定步骤，已经提出了用于烷基化反应的自由基途径。值得注意的是，本方案具有优异的官能团公差，并且可以以良好的效率轻松扩大。

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来源
《Chemistry: A European journal》 |2017年第37期|共4页
作者
Jiangwei Wen; Fan Zhang; Wenyan Shi; Aiwen Lei;
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作者单位

Institute for Advanced Studies (IAS) College of Chemistry and Molecular Sciences Wuhan University Wuhan 430072 Hubei (P. R. China);

Institute for Advanced Studies (IAS) College of Chemistry and Molecular Sciences Wuhan University Wuhan 430072 Hubei (P. R. China);

Institute for Advanced Studies (IAS) College of Chemistry and Molecular Sciences Wuhan University Wuhan 430072 Hubei (P. R. China);

Institute for Advanced Studies (IAS) College of Chemistry and Molecular Sciences Wuhan University Wuhan 430072 Hubei (P. R. China);

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原文格式 PDF
正文语种 eng
中图分类应用化学;
关键词
alkylation; C-H activation; internal olefins; metalfree; cross-coupling;

机译：烷基化;C-H激活;内烯烃;金属非法;交叉耦合;

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1. Metal-Free Direct Alkylation of Ketene Dithioacetals by Oxidative C(sp~2)-H/C(sp~3)-H Cross-Coupling [J] . Jiangwei Wen, Fan Zhang, Wenyan Shi, Chemistry: A European journal . 2017,第37期

机译：通过氧化C（SP〜2）-H / C（SP〜3）-H交叉耦合的无金属直接烷基化酮二缩醛
2. Transition Metal-Free Oxidative Cross-Coupling C(sp(2))-C(sp(3)) Bond Formation: Regioselective C-3 Alkylation of Coumarins with Tertiary Amines [J] . Dian Longyang, Zhang-Negrerie Daisy, Du Yunfei Advanced synthesis & catalysis . 2017,第18期

机译：无金属无金属氧化交联C（SP（2）） - C（SP（3））键形成：具有叔胺的香豆苷的区域选择性C-3烷基化
3. 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-Mediated C(sp(2))-C(sp(3)) Cross-Dehydrogenative Coupling Reaction: alpha-Alkylation of Push-Pull Enamines and alpha-Oxo Ketene Dithioacetals [J] . Cheng Dongping, Wu Lijun, Deng Zhiteng, Advanced synthesis & catalysis . 2017,第24期

机译：2,3-二氯-5,6-二氰基1,4-苯并醌（DDQ）介导的C（SP（2）） - C（SP（3））交叉脱氢偶联反应：推拉的α-烷基化烯氨酸和α-氧代酮二缩醛
4. Ni/Co-Catalyzed C(sp~3)-C(sp~3) Cross-Coupling Using Alkyl Tosylates as Radical Sources [C] . Takuya Michiyuki, Itaru Osaka, Kimihiro Komeyama 日本化学会春季年会講演予稿集 . 2018

机译：Ni /助催化的C（SP〜3）-C（SP〜3）使用烷基甲磺酸盐作为自由基来源的交叉偶联
5. Metal-Free Sulfoxide-Directed Cross-Coupling [D] . ?Yang, Kevin 2019

机译：无金属亚砜定向交叉偶联
6. Metal-free direct alkylation of unfunctionalized allylic/benzylic sp3 C–H bonds via photoredox induced radical cation deprotonation [O] . Rong Zhou, Haiwang Liu, Hairong Tao, 2017

机译：通过光氧化还原诱导的自由基阳离子去质子化作用使未官能化的烯丙基/苄基sp3 C–H键无金属直接烷基化
7. Direct C(sp2)-H chlorination of ketene dithioacetals using FeCl3 as the chloride source and PhI(OAc)2 as an oxidant [O] . XianYu Meng, ZhongXue Fang, Badru-Deen Barry, 2012

机译：使用FeCl3作为氯化物源和PhI（OAc）2作为氧化剂直接对乙烯酮二硫缩醛进行C（sp2）-H氯化

Metal-Free Direct Alkylation of Ketene Dithioacetals by Oxidative C(sp~2)-H/C(sp~3)-H Cross-Coupling

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