A cleaner approach to solid-supported radical chemistry: Application of hypophosphite salts to intramolecular C-C bond formation on the solid-phase

Synlett

Volumn , Issue 3, 2005, Pages 477-480

  Chevet, Caroline ^a   Jackson, Toby ^a   Santry, Barbara ^a   Routledge, Anne ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

Author keywords

Cyclizations; Radical reactions; Solid phase

Indexed keywords

HYPOPHOSPHITE SALT; PHOSPHITE; RADICAL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMISTRY; CYCLIZATION; PHASE TRANSITION; SOLID STATE;

EID: 14644420179     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-862376     Document Type: Article

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12. 2 (3 × 5 mL) then dried under vacuum for 48 h.
13. +) then analysed by HPLC on a Alltech econosil Si column eluting with hexane-i-PrOH (0-5 min 100% hexane, 5-35 min gradient 0-30% i-PrOH): iodoether 2, 18.4 min; benzyl ether 3, 17.3 min; benzofuran 4, 19.9 min; 220 nm detection.
14. 2,2′-azobis(2-amidinopropane) dihydrochloride, a water soluble azo radical initiator.
15. The stepwise solid-phase synthesis (Scheme 1) could not be applied to NovaSyn® TG carboxy resin as reaction with cis-butan-1,4-diol resulted in extensive cross-linking of the resin.
16. 2 (3 × 5 mL) then dried under vacuum for 48 h.
17. Carboxy-functionalised resins were either commercially available (HypoGel®) or synthesized from commercially available amino functionalised resin by reaction with glutaric anhydride (JandaJel®, ArgoGel® and ArgoPore®).
18. -1 loading = 1.5 mL solvent for reaction), 1 equiv of initiator added at t = 0 h and t = 24 h.