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Issue 41, 2020
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Potassium tert-butoxide mediated C–C, C–N, C–O and C–S bond forming reactions

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Abstract

Potassium tertiary butoxide (KOtBu) mediated constructions of C–C, C–O, C–N, and C–S bonds are reviewed with special emphasis on their synthetic applications. KOtBu can be used to perform reactions already known to be carried out using transition metals, but it has advantages in terms of environmental congruence and economic cost. KOtBu is widely employed in organic synthesis to mediate the construction of C–C, C–O, C–N, C–S and miscellaneous bonds in good to excellent yields. Synthetic uses of KOtBu in coupling, alkylation, arylation, α-phenylation, cyclization, Heck-type, annulation, photo-arylation, aromatic-substitution, amidation, and silylation reactions are summarized and discussed. The mechanisms through which KOtBu carries out a specific reaction are also discussed. One of the goals of this review is to attract the attention of chemists as to the benefits of using KOtBu as an environmentally benign alternative to transition metals and its applications in the construction of chemical bonds with predominant importance in organic synthesis. This review completely covers the synthetic protocols that have been performed using KOtBu in the last two decades.

Graphical abstract: Potassium tert-butoxide mediated C–C, C–N, C–O and C–S bond forming reactions

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Article information


Submitted
06 Jul 2020
Accepted
13 Aug 2020
First published
01 Sep 2020

Org. Biomol. Chem., 2020,18, 8346-8365
Article type
Review Article

Potassium tert-butoxide mediated C–C, C–N, C–O and C–S bond forming reactions

J. Madasu, S. Shinde, R. Das, S. Patel and A. Shard, Org. Biomol. Chem., 2020, 18, 8346
DOI: 10.1039/D0OB01382J

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