Research Progress of Suzuki-Miyaura Cross-Coupling Reaction Mechanism

doi:10.6023/cjoc202103040

Abstract

During the past several decades, Suzuki-Miyaura cross-coupling reaction has emerged and flourished as one of the most remarkable and practical methods to construct C—C bond. The substrates, organoboronic compounds, are usually more stable, less toxic and easier to obtain compared with other metal or metalloid alternatives. Suzuki-Miyaura cross-coupling reaction possesses extraordinary merits of demonstrated efficiency, broad functional group compatibility and mild reaction conditions. It has been the premier method to construct C—C bond for organic synthetic chemists and has been widely applied in the industrial syntheses. The rapid development of Suzuki-Miyaura cross-coupling reaction is accompanied with the progress of mechanism studies. It is well accepted that the catalytic cycle of Suzuki-Miyaura cross-coupling reaction contains three main steps: oxidative addition of organic halides to Pd catalysts, transmetalation between oxidative addition intermediates and organoboronic compounds, and reductive elimination from transmetalation intermediates to form C—C bond along with regenerating Pd catalysts. However, these three main steps can be influenced by diverse reaction conditions, and different reaction pathways may occur within each single step. Furthermore, beyond the oxidative addition and transmetalation intermediates, other transient but crucial intermediates may exist. To figure out these issues and discover more insights into Suzuki- Miyaura cross-coupling reaction, numerous researchers have designed and conducted systematic investigations. Herein, the recent progress of mechanism studies is summarized and discussed. The steps of oxidative addition, transmetalation and reductive elimination are discussed in detail. Moreover, a brief introduction of transition-metal-free and base-free Suzuki- Miyaura cross-coupling reactions which show more possibilities of the reaction mechanism is given. Besides summary of precedent research works, our opinions about future development of the mechanism studies are also given. Although breakthroughs have been made in the mechanism studies, further investigations are needed to bring comprehensive knowledge of this reaction and help us further optimize the reaction conditions.

Key words: Suzuki-Miyaura cross-coupling reaction, mechanism study, oxidative addition, transmetalation, pre-transmetala- tion, reductive elimination

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Lei Zhang, Chen Yang, Xuefeng Guo, Fanyang Mo. Research Progress of Suzuki-Miyaura Cross-Coupling Reaction Mechanism[J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3492-3510.

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Fig. & Tab. 29

Scheme 1. Catalytic cycle of Suzuki-Miyaura cross-coupling reaction

Scheme 2. Oxidative addition mechanisms of polar reagents (superscript of M meaning valence states)

Scheme 3. Suzuki-Miyaura cross-coupling reaction of alkyl iodides and organoboranes

Scheme 4. Difluoroalkylation of aryl boronic acids

Scheme 5. Synthesis of Pd(Ⅳ) oxidative addition intermediates

Scheme 6. Norbornene involved Pd(Ⅱ)/Pd(Ⅳ) cycle

Scheme 7. Pd(Ⅳ) intermediates involved racemized cross-coupling

Scheme 8. Report of Pd catalysts containing pincer ligand from Iwasa and co-workers

Scheme 9. Report of Pd catalysts containing pincer ligand from Frech and co-workers

Scheme 10. Application of abnormal NHC-Pd complexes in Suzuki-Miyaura cross-coupling reactions

Scheme 11. Transmetalation process

Scheme 12. Preliminary investigation of pre-transmetalation intermediates

Scheme 13. Attempts of detecting pre-transmetalation intermediates via NMR

Scheme 14. Synthesis of pre-transmetalation intermediates

Scheme 15. Path A and path B of transmetalation

Entry	Reaction time/h	Reactant	Product	Yield/%
1	1	Bu-9-BBN	Ph-Bu	40
1	1	Hex-9-BBN	Ph-Hex	48
2	12	Hex-9-BBN	Ph-Hex	86
2	12	Bu-OBBN	Ph-Bu	0
3	12	Bu-9-BBN	Ph-Bu	84
3	12	Hex-OBBN	Ph-Hex	0
4	12	Bu-OBBN	Ph-Bu	44
4	12	Hex-OBBN	Ph-Hex	49

Table 1. Comparison of R-9-BBN and R-OBBD in reaction activity

Scheme 16. Mechanism of reactions related to R-9-BBN and R-OBBD

Scheme 17. Distinction of reaction pathways facilitated by electrochemical techniques

Scheme 18. Influence of fluorinion and alkali metal cation on transmetalation

Scheme 19. Kinetic studies of stoichiometric reactions

Scheme 20. Kinetic studies of model reactions

Scheme 21. Activation parameters of transmetalation process and effect of phosphine ligands on reaction rate

Scheme 22. Autocatalysis in transmetalation

Scheme 23. Influence of boronic esters on transmetalation process

Scheme 24. Reductive elimination of trans-diarylpalladium complexes

Scheme 25. Reductive elimination of cis-diarylpalladium complexes

Scheme 26. Influence of anions on reductive elimination

Scheme 27. Transition-metal-free Suzuki-Miyaura cross-coupling reactions

Scheme 28. Base-free Suzuki-Miyaura cross-coupling reactions

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Suzuki-Miyaura偶联反应机理研究进展