New Dimensions of Brønsted Base Catalyzed Carbon–Carbon Bond-Forming Reactions

Synlett ◽  
2020 ◽  
Vol 32 (01) ◽  
pp. 14-22
Author(s):  
Yasuhiro Yamashita ◽  
Shū Kobayashi

Catalytic carbon–carbon bond-forming reactions of weakly acidic carbon pronucleophiles (pK a in DMSO ≥30) were developed using strong alkaline metal Brønsted bases as catalysts. Not only weakly acidic amides, esters, nitriles, sulfonamides without any activating group, and alkyl azaarenes, but also alkyl arenes such as toluene, were applicable for the reactions, which are difficult to be applied in typical Brønsted base catalyzed reactions. Expansion to enantioselective reactions was also revealed to be possible. The reactions are atom economical and require only inexpensive alkaline metals rather than precious transition metals.1 Introduction2 Catalytic Direct-Type Addition Reactions of Weakly Acidic Carbonyl and Related Pronucleophiles3 Catalytic Direct-Type Addition Reactions of Alkyl Azaarenes4 Catalytic Direct-Type Addition Reactions of Alkyl Arenes5 Conclusion

2022 ◽  
Author(s):  
Yasuhiro Yamashita

Chiral alkaline metal Brønsted bases are traditional and reliable promoters in enantioselective catalysis. Here, new chiral potassium strong base catalysts were developed for enantioselective carbon–carbon bond-forming reactions of weakly acidic...


2019 ◽  
Vol 16 (9) ◽  
pp. 689-696
Author(s):  
Animesh Roy ◽  
Bilal A. Bhat ◽  
Salvatore D. Lepore

Organometallic moieties attached to substrates via π-complexation play an important role as auxiliaries. As described in the present review, η-linked auxiliaries have been employed to overcome numerous synthesis obstacles that continue to present significant challenges for catalyzed reactions. This has been particularly true in carbon-carbon bond forming reactions involving highly unsaturated systems such as arenes, dienes and allenes, which are emphasized here.


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