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Multifunctional Linkers as an Efficient Tool for the Synthesis of Diverse Small Molecule Libraries: The Triazene Anchors

Publisher Summary Triazenes provide new possibilities for the activation of the ortho-position of arenes by coordination of metal ions and/or by lowering the electron density of the arene ring, they are also ideal synthons for diazonium salts. This chapter discusses two linkers based on the triazene chemistry, T 1 and T 2, used for the synthesis of diverse small molecule libraries. While the T 1 linker system consists of 3,3-dialkyl-1 aryl triazene bound to the support via the alkyl chain, the T 2 linker family is based on immobilized aryl diazonium salts. The triazene T 1 linker has been successfully used as a linker for arenes. While the T 1 linker involves an immobilization of a diazonium salt on an amine resin, the T 2 linker represents the reversal of this concept. The T2 linker has recently been shown to be a versatile backbone amide anchor. Immobilized disubstituted triazenes were acylated with carboxylic acid anhydrides or chlorides to give amide derivatives. These amides were cleaved under very mild conditions using trimethyl chlorosilane. This sequence thus, employs the T 2 system as backbone amine linker and was demonstrated in the automated library synthesis of substituted amide derivatives.

Multifunctional Linkers as an Efficient Tool for the Synthesis of Diverse Small Molecule Libraries: The Triazene Anchors

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Multifunctional Linkers as an Efficient Tool for the Synthesis of Diverse Small Molecule Libraries: The Triazene Anchors

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Multifunctional Linkers as an Efficient Tool for the Synthesis of Diverse Small Molecule Libraries: The Triazene Anchors