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New Dimensions of Brønsted Base Catalyzed Carbon–Carbon Bond-Forming Reactions
Synlett ( IF 1.7 ) Pub Date : 2020-08-11 , DOI: 10.1055/s-0040-1707202
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 Bronsted 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 Bronsted 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 Introduction 2 Catalytic Direct-Type Addition Reactions of Weakly Acidic Carbonyl and Related Pronucleophiles 3 Catalytic Direct-Type Addition Reactions of Alkyl Azaarenes 4 Catalytic Direct-Type Addition Reactions of Alkyl Arenes 5 Conclusion

中文翻译:

布朗斯特碱催化碳-碳键形成反应的新维度

使用强碱金属布朗斯台德碱作为催化剂开发了弱酸性碳亲核试剂(DMSO 中的 pK a ≥30)的催化碳-碳键形成反应。不仅弱酸性酰胺、酯、腈、没有任何活化基团的磺酰胺和烷基氮杂芳烃,而且诸如甲苯等烷基芳烃都适用于这些在典型的布朗斯台德碱催化反应中难以应用的反应。对映选择性反应的扩展也被证明是可能的。这些反应是原子经济的,只需要廉价的碱金属而不是贵重的过渡金属。
更新日期:2020-08-11
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