Wilkins Lewis C, Santi Nicolò, Luk Louis Y P, Melen Rebecca L
School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, UK.
School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, UK
Philos Trans A Math Phys Eng Sci. 2017 Aug 28;375(2101). doi: 10.1098/rsta.2017.0009.
The combination of 1-benzyl-1,4-dihydropyridines with the strong Lewis acid, B(CF), generates a stable pyridinium borohydride species in high yields (94%) in as little as 10 min. This use of biologically inspired hydride sources further builds on the recent work of new hydride donors in the formation of borohydrides. When functionalizing the dihydropyridine with an amide or carboxylic acid moiety, a disproportionation reaction composed of a series of protonation/reduction steps is observed upon the addition of B(CF) As a result, one equivalent of dihydropyridine undergoes net hydrogenation, whereas the other is dehydrogenated yielding the pyridinium counterpart in a transfer hydrogenation-type mechanism.This article is part of the themed issue 'Frustrated Lewis pair chemistry'.
1-苄基-1,4-二氢吡啶与强路易斯酸B(CF) 相结合，在短短10分钟内就能以94%的高产率生成稳定的硼氢吡啶鎓物种。这种受生物启发的氢化物源的使用进一步建立在新型氢化物供体在硼氢化物形成方面的最新研究基础之上。当用酰胺或羧酸部分对二氢吡啶进行官能化时，加入B(CF) 后会观察到由一系列质子化/还原步骤组成的歧化反应。结果，一当量的二氢吡啶发生净氢化反应，而另一当量则脱氢，通过转移氢化型机制生成吡啶鎓对应物。本文是主题为“受阻路易斯对化学”的特刊的一部分。
