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Radical Chemistry on Solid Support

  • Andrea M. McGhee
  • David J. ProcterEmail author
Chapter
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 264)

Abstract

This review covers recent advances in the field of radical chemistry on solid phase. Intermolecular processes using both immobilized radicals with solution-phase acceptors and immobilized acceptors with radicals in solution are discussed, as are radical cyclization reactions on polymer supports. Progress in the development of solid-phase asymmetric radical processes and the design of linkers cleaved by radical processes are also discussed.

Radicals Solid phase Linkers Supported reagents 

Abbreviations

Ac

Acetyl

ACCN

1,1′-Azobis(cyclohexanecarbonitrile)

AIBN

2,2′-Azobis(2-methylpropionitrile)

Bn

Benzyl

Boc

t-Butoxycarbonyl

Bz

Benzoyl

CAN

Ceric ammonium nitrate

Cbz

Benzyloxycarbonyl

Cy

Cyclohexyl

DAST

Diethylaminosulfur trifluoride

DCC

1,3-Dicyclohexyl carbodiimide

DCE

Dichloroethane

DEAD

Diethyl azodicarboxylate

DIAD

Diisopropyl azodicarboxylate

DIC

1,3-Diisopropyl carbodiimide

DMAP

4-Dimethylaminopyridine

DMF

N,N-Dimethylformamide

DMPU

1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone

DMSO

Dimethylsulfoxide

Fmoc

9-Fluorenylmethoxycarbonyl

HASC

α Heteroatom-substituted carbonyl

HBTU

N,N,N′,N′-Tetramethyl-O-(1H-benzotriazol-1-yl)uronium hexafluorophosphate

HMPA

Hexamethylphosphoramide

HOBt

1-Hydroxybenzotriazole

mCPBA

3-Chloroperbenzoic acid

MOM

Methoxymethyl

Ms

Methanesulfonyl

MW

microwave

NEM

N-Ethylmaleimide

NMM

N-Methylmorpholine

NMP

1-Methyl-2-pyrrolidone

PEG

Poly(ethylene glycol)

Phth

Phthalate

PMB

4-Methoxybenzyl

PTSA

p-Toluene sulfonic acid

ROMP

Ring opening metathesis polymerization

TBDMS

t-Butyldimethylsilyl

TBDPS

t-Butyldiphenylsilyl

TBS

t-Butyldimethylsilyl

TFA

Trifluoroacetic acid

THF

Tetrahydrofuran

THP

Tetrahydropyranyl

TMS

Trimethylsilyl

Ts

4-Toluenesulfonyl

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Authors and Affiliations

  1. 1.The School of ChemistryUniversity of ManchesterManchesterUK

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