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. 2020 Mar 17;10(18):10883-10887.
doi: 10.1039/d0ra02016h. eCollection 2020 Mar 11.

Solvent-free and room temperature microwave-assisted direct C7 allylation of indolines via sequential C-H and C-C activation

Qiuling Wang  1 , Linlin Shi  1 , Shuang Liu  1 , Changlei Zhi  1 , Lian-Rong Fu  1 , Xinju Zhu  1 , Xin-Qi Hao  1 , Mao-Ping Song  1
Affiliations

Solvent-free and room temperature microwave-assisted direct C7 allylation of indolines via sequential C-H and C-C activation

Qiuling Wang et al. RSC Adv. .

Abstract

A Ru or Rh-catalyzed efficient and atom-economic C7 allylation of indolines with vinylcyclopropanes was developed via sequential C-H and C-C activation. A wide range of substrates were well tolerated to afford the corresponding allylated indolines in high yields and E/Z selectivities under microwave irradiation. The obtained allylated indolines could further undergo transformations to afford various value-added chemicals. Importantly, this reaction proceeded at room temperature under solvent-free conditions.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Scheme 1
Scheme 1. Sequential C–H/C–C activations using VCPs.
Scheme 2
Scheme 2. Gram-scale reaction and further derivatization of product 3aa.
Scheme 3
Scheme 3. Control experiments.
Scheme 4
Scheme 4. Proposed reaction mechanism.
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