Advances on Directing-Group Assisted meta-C-H Functionalization Catalyzed by Transition Metal

doi:10.6023/cjoc201903029

Abstract

Transition-metal-catalyzed functionalization of unactivated C-H bonds is a highly attractive strategy for the synthesis of organic molecules, however, regioselective control is a central challenge in this field. The directing group assisted C-H functionalizations such as the use of directing templates and transient mediator, secondary interaction have attracted more attentions from researchers. The meta-C-H functionalizatioin assisted by directing groups are summarized in details. The existing problems and limitations of this field are also included. Finally, the development trend of this area is prospected.

Key words: directed by template, meta-activation, C-H functionalization, secondary interaction, transient mediator

Cite this article

Wu Mei, Huang Xinping, Zhang Haibing, Li Pengfei. Advances on Directing-Group Assisted meta-C-H Functionalization Catalyzed by Transition Metal[J]. Chinese Journal of Organic Chemistry, 2019, 39(11): 3114-3131.

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Fig. & Tab. 20

Figure 1. U template and transition state of meta-C—H activation

Figure 2. Transition state of benzyl ether derivatives of meta- C—H activation and Ψ3

Figure 3. meta-C—H activation transition state of 3-phenyl- propanoic acid derivatives

Scheme 1. Meta-arylation of 3-phenylpropanoic acid and phenolic derivatives

Scheme 2. meta-Olefination of benzylsulfonyl ester derivatives

Scheme 3. meta-Diolefination of 2-phenyl ethanesulfonic acid and 3-phenylpropanoic acid derivatives

Scheme 4. meta-Olefination of benzyl silane derivatives

Scheme 5. Meta-olefination of biphenyl phenol and biphenyl carboxylic acid derivatives

Figure 4. Transition state in meta-activation of phenyl alcohols

Scheme 6. meta-C—H activation directed by pyrimidine-based template

Scheme 7. meta-C—H activation directed by transient mediator

Scheme 8. meta-C—H arylation of phenylamine, phenol and heterocycle phenylamine

Scheme 9. meta-C—H arylation and ethylation of benzyl alcohol derivatives

Scheme 10. Hydrogen bond accelerated meta-C—H activation

Figure 5. Design of ligand to accelerate the reaction

Scheme 11. Interaction between Lewis acid and base accelerated meta-C—H activation

Scheme 12. Electrostatic interaction accelerated meta-C—H activation

Scheme 13. Ion pair accelerated meta-C—H activation

Scheme 14. Hydrogen bond accelerated meta-C—H activation

Scheme 15. Interaction between π bond and cationic accelerated meta-C—H activation

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