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Advances of KOtBu-Involved Reactions in Organic Synthesis From 2020 to 2025
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DOI：10.1002/tcr.70225.png)
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Abstract
En 中文
Potassium tert-butoxide (KOtBu), a strong non-nucleophilic base with a pKa value of 17.5, has emerged as a versatile and indispensable reagent in modern organic synthesis. Notably, KOtBu can promote a wide range of bond-forming transformations that conventionally rely on transition-metal catalysis, enabling the efficient construction of carbon–carbon (CC), carbon–heteroatom (CX), and heteroatom–heteroatom (XY) bonds under relative mild reaction conditions. KOtBu-mediated reactions predominantly proceed via two well-established mechanistic pathways, namely ionic and radical manifolds, wherein the reactivity of key intermediates is highly dependent on reaction conditions and exogenous additives. Compared to transition-metal catalysts, KOtBu offers prominent advantages in terms of economic cost and environmental compatibility. In this review, we systematically summarize recent advances in KOtBu-involved reactions, covering the construction of carbon–carbon (CC), carbon–nitrogen (including CN and CONH), carbon–oxygen (CO), carbon–silicon (CSi), as well as miscellaneous bonds including carbon–sulfur (CS), carbon–seleno (CSe), carbon–iodo (CI), carbon–deuterium (CD), etc. We focus on reaction development, plausible mechanistic pathways, and potential synthetic applications of these protocols in the synthesis of pharmaceuticals, agrochemicals, and functional materials. This review aims to provide an up-to-date overview of KOtBu-enabled organic transformations for organic, medicinal, and materials chemists, and to facilitate further exploration and expansion of their synthetic utility.
Keywords:
C<span class='icomoon'>?</span>C bond formation
C<span class='icomoon'>?</span>X (X = N, O/S, Si, etc.) bond formation
KOtBu
reaction mechanism and application
transition-metal-free (TM-free)
Journal
IF:
7.5
Papers:
2.1K
Citations:
9.3K
Organization
Cited Papers