Noncovalent solid-phase organic synthesis (NC-SPOS) is a form of

solid-phase synthesis In chemistry, solid-phase synthesis is a method in which molecules are covalently bound on a solid support material and synthesised step-by-step in a single reaction vessel utilising selective protecting group chemistry. Benefits compared with ...

whereby the organic

substrate Substrate may refer to: Physical layers *Substrate (biology), the natural environment in which an organism lives, or the surface or medium on which an organism grows or is attached ** Substrate (aquatic environment), the earthy material that exi ...

is bonded to the

solid phase In the physical sciences, a phase is a region of material that is chemically uniform, physically distinct, and (often) mechanically separable. In a system consisting of ice and water in a glass jar, the ice cubes are one phase, the water is a ...

not by a

covalent bond A covalent bond is a chemical bond that involves the sharing of electrons to form electron pairs between atoms. These electron pairs are known as shared pairs or bonding pairs. The stable balance of attractive and repulsive forces between atom ...

but by other chemical interactions.

Synthesis

This bond may consist of an

induced dipole interaction In molecular physics and chemistry, the van der Waals force (sometimes van der Waals' force) is a distance-dependent interaction between atoms or molecules. Unlike ionic or covalent bonds, these attractions do not result from a chemical elect ...

between a

hydrophobic In chemistry, hydrophobicity is the chemical property of a molecule (called a hydrophobe) that is seemingly repelled from a mass of water. In contrast, hydrophiles are attracted to water. Hydrophobic molecules tend to be nonpolar and, thu ...

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 A solvent (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for p ...

releases the organic substrate containing the anchor. In one experimental setup the hydrophobic matrix is RP silica gel (C₁₈) and the anchor is

acridone Acridone is an organic compound based on the acridine skeleton, with a carbonyl group at the ''9'' position. Synthesis and structure The molecule is planar. Optical spectra reveal that the keto tautomer predominates in the gas-phase and in ethanol ...

. Acridone is N-alkylated and the

terminal alkene In organic chemistry, terminal alkenes (alpha-olefins, α-olefins, or 1-alkenes) are a family of organic compounds which are alkenes (also known as olefins) with a chemical formula , distinguished by having a double bond at the primary, alpha ( ...

group is converted into an

aldehyde In organic chemistry, an aldehyde () (lat. ''al''cohol ''dehyd''rogenatum, dehydrogenated alcohol) is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred ...

ozonolysis In organic chemistry, ozonolysis is an organic reaction where the Saturated and unsaturated compounds, unsaturated bonds are Bond cleavage, cleaved with ozone (). Multiple carbon–carbon bond are replaced by carbonyl () groups, such as aldehydes ...

. 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 Green chemistry, similar to sustainable chemistry or circular chemistry, is an area of chemistry and chemical engineering focused on the design of products and processes that minimize or eliminate the use and generation of hazardous substances. Wh ...

) and the second reaction is a

Sonogashira coupling The Sonogashira reaction is a cross-coupling reaction used in organic synthesis to form carbon–carbon bonds. It employs a palladium catalyst as well as copper co-catalyst to form a carbon–carbon bond between a terminal alkyne and an aryl or vi ...

. Substrates may vary in these sequences and in this way a

chemical library A chemical library or compound library is a collection of stored chemicals usually used ultimately in high-throughput screening or industrial manufacture. The chemical library can consist in simple terms of a series of stored chemicals. Each chemi ...

of new compounds can be realized. {{center, The phosphorus ligand in the

with phenyliodine is the water-soluble TPPTS ligand

References

Solid-phase synthesis