Radical addition-polar termination cascade: efficient strategy for photoredox-neutral-catalysed cyclopropanation and Giese-type reactions of alkenyl N-methyliminodiacetyl boronates,Organic Chemistry Frontiers

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Radical addition-polar termination cascade: efficient strategy for photoredox-neutral-catalysed cyclopropanation and Giese-type reactions of alkenyl N-methyliminodiacetyl boronates
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2020-05-26 , DOI: 10.1039/d0qo00349b
Yongjun Liu _{1,

2,

3,

4} , Wenping Luo _{1,

2,

3,

4} , Jiali Wu _{4,

5,

6,

7} , Yewen Fang _{4,

5,

6,

7} , Yan Li _{1,

2,

3,

4} , Xiaoping Jin _{4,

8,

9,

10} , Li Zhang _{4,

8,

9,

10} , Zongyong Zhang _{4,

5,

6,

7} , Fenfen Xu _{4,

5,

6,

7} , Chan Du _{4,

5,

6,

7}

Affiliation

With radical addition-polar termination (RAPT) cascade as the strategy, efficient cyclopropanation and Giese-type reactions of alkenyl N-methyliminodiacetyl boronates have been realized by means of photoredox catalysis. With chloro- or bromomethyl silicate as the methylene source, a variety of cyclopropyl MIDA boronates as air- and chromatographically stable solids were prepared via photoredox-catalysed cyclopropanation of α-MIDA-boryl styrenes, 2-propenyl-BMIDA, and ethenyl-BMIDA. Moreover, photocatalytic Giese-type reactions of alkyl radicals with α-MIDA-boryl styrenes were also developed. It is essential for the successful radical conjugate addition employing alkyl silicates as the radical precursor. These RAPT cascades are characterized by a redox-neutral and additive-free process.

中文翻译：

自由基加成-极性终止级联：烯基N-甲基亚氨基二乙酰基硼酸酯的光氧化还原中性催化环丙烷化和Giese型反应的有效策略

以自由基加成-极性终止（RAPT）级联为策略，已经通过光氧化还原催化实现了烯基N-甲基亚氨基二乙酰基硼酸酯的有效环丙烷化和Giese型反应。以氯或溴代甲基丙烯酸硅作为亚甲基源，通过以下方法制备了多种环丙基MIDA硼酸酯，它们是空气和色谱稳定的固体光氧化还原催化的α-MIDA-硼苯乙烯，2-丙烯基-BMIDA和乙烯基-BMIDA的环丙烷化。此外，还开发了烷基与α-MIDA-硼苯乙烯的光催化吉斯型反应。对于使用烷基硅酸盐作为自由基前体的成功的自由基共轭加成，这是必不可少的。这些RAPT级联的特征是氧化还原中性且无添加剂。

更新日期：2020-06-30

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