Alcohols, click chemistry

By combining several click reactions, click chemistry allows for the rapid synthesis of useful new compounds of high complexity and combinatorial libraries. The 2-type reaction of the azide ion with a variety of epoxides to give azido alcohols has been exploited extensively in click chemistry. First of all, azido alcohols can be converted into amino alcohols upon reduction.70 On the other hand, aliphatic azides are quite stable toward a number of other standard organic synthesis conditions (orthogonality), but readily undergo 1,3-dipolar cycloaddition with alkynes. An example of the sequential reactions of... 

Recently propargyl alcohols were reported to undergo FeCb-catalyzed triazole propargylation to yield propargylated triazoles. A mixture of N-2 and N-1 isomers is generally produced. The products of the reaction were then further derivatized via click chemistry to synthesize bis-triazole systems. 

Among these reactions, the Cu(l)-catalyzed azide-alkyne cycloaddition (CuAAC) is the most widely used. This reaction has been implemented for the preparation of segmented block copolymers from polymerizable monomers by different mechanisms. For example, Opsteen and van Hest [22] successfully prepared poly(ethylene oxide)-b-poly(methyl methacrylate) (PEO-b-PMMA) and PEO-b-PSt by using azide and alkyne end-functionalized homopolymers as the click reaction components (Scheme 11.2). Here, PEO, PSt, and PMMA homopolymers were obtained via living anionic ring-opening polymerization (AROP), atom transfer radical polymerization (ATRP), and postmodification reactions. Several research groups have demonstrated the combination of different polymerization techniques via CuAAC click chemistry, in the synthesis of poly(e-caprolactone)-b-poly(vinyl alcohol) (PCL-b-PVA)... 

Scheme 2.61 Preparation of strongly related alcohols by click chemistry.

Scheme 2.98 Synthesis of monodentate phosphite starting from alcohols derived by means of click chemistry.

Ossipov DA, Hilbom J (2006) Poly(vinyl alcohol)-based hydrogels formed by click chemistry . Macromolecules 39 1709-1718... 

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