View source for Noncovalent solid-phase organic synthesis

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'''Noncovalent solid-phase organic synthesis''' ('''NC-SPOS''') is a form of [[solid-phase synthesis]] whereby the [[organic compound|organic]] [[substrate (chemistry)|substrate]] is bonded to the [[solid phase]] not by a [[covalent bond]] but by other chemical interactions.

==Synthesis==
This bond may consist of an [[induced dipole interaction]] between a [[hydrophobic]] matrix and a hydrophobic anchor. As long as the reaction medium is hydrophilic (polar) in nature the anchor will remain on the solid phase. Switching to a [[nonpolar solvent]] releases the organic substrate containing the anchor.  

In one experimental setup<ref>{{cite journal |vauthors = Porzelle A, Fessner WD |year=2005 |title=Reversible Substrate Anchoring: NC-SPOS as a Sustainable Approach to Solid-Supported Organic Synthesis |journal=[[Angewandte Chemie International Edition]] |volume=44 |issue=30 |pages=4724–4728 |doi=10.1002/anie.200462278 |url=http://www3.interscience.wiley.com/cgi-bin/abstract/110544202/ABSTRACT |archive-url=https://archive.today/20110812231642/http://www3.interscience.wiley.com/cgi-bin/abstract/110544202/ABSTRACT |url-status=dead |archive-date=2011-08-12 |accessdate=2006-09-26 |format=abstract |pmid=15968704|doi-access=free }}</ref> the hydrophobic matrix is [[reversed-phase chromatography|RP silica gel]] (C<sub>18</sub>) and the anchor is [[acridone]]. Acridone is N-alkylated and the [[terminal alkene]] group is converted into an [[aldehyde]] by [[ozonolysis]]. This compound is bonded to RP silica gel and this system is subjected to a tandem sequence of organic reactions. The first reaction is a [[Barbier reaction]] with propargylic bromide in water ([[green chemistry]]) and the second reaction is a [[Sonogashira coupling]]. Substrates may vary in these sequences and in this way a [[chemical library]] of new compounds can be realized.

[[Image:NC STOS.gif|center|Noncovalent solid-phase organic synthesis]]

{{center|<small>The phosphorus ligand in the [[Sonogashira coupling]] with phenyliodine is the water-soluble [[TPPTS ligand]] </small>}}

== References ==
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[[Category:Solid-phase synthesis]]