514826-78-9

Basic information

• Product Name: 2-iodo-1,3-phenylene bis(trifluoromethanesulfonate)
• Synonyms: 2-iodo-1,3-phenylene bis(trifluoromethanesulfonate)
• CAS NO: 514826-78-9
• Molecular Weight: 500.135
• Mol File: 514826-78-9.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 2-iodo-1,3-phenylene bis(trifluoromethanesulfonate)(CAS DataBase Reference)
• NIST Chemistry Reference: 2-iodo-1,3-phenylene bis(trifluoromethanesulfonate)(514826-78-9)
• EPA Substance Registry System: 2-iodo-1,3-phenylene bis(trifluoromethanesulfonate)(514826-78-9)

Safety Data

• Hazardous Substances Data: 514826-78-9(Hazardous Substances Data)

Upstream product

• 358-23-6 trifluoromethylsulfonic anhydride 
• 108-46-3 recorcinol 
• 41046-67-7 2-iodoresorcinol 

Downstream Products

• 1402160-68-2 C₁₁H₁₀F₃IO₄S 
• 169615-68-3 5-(benzyloxy)bicyclo[4.2.0]octa-1⁽⁶⁾,2,4-trien-7-one 

Relevant articles and documents

Concise Synthesis of (-)-Cycloclavine and (-)-5- epi-Cycloclavine via Asymmetric C-C Activation

To illustrate the synthetic significance of C-C activation methods, here we describe an efficient strategy for the enantioselective total syntheses of (-)-cycloclavine and (-)-5-epi-cycloclavine, which is enabled by an asymmetric Rh-catalyzed cut-and-sew transformation between benzocyclobutenones and olefins. Despite the compact structure of cycloclavine with five-fused rings, the total synthesis was accomplished in 10 steps with a 30% overall yield. Key features of the synthesis include (1) a Pd-catalyzed tandem C-N bond coupling/allylic alkylation sequence to construct the nitrogen-tethered benzocyclobutenone, (2) a highly enantioselective Rh-catalyzed carboacylation of alkenes to forge the indoline-fused tricyclic structure, and (3) a diastereoselective cyclopropanation for preparing the tetrasubstituted cyclopropane ring. Notably, an improved catalytic condition has been developed for the nitrogen-tethered cut-and-sew transformation, which uses a low catalyst loading and allows for a broad substrate scope with high enantioselectivity (94-99% e.e.). The C-C activation-based strategy employed here is anticipated to have further implications for syntheses of other natural products that contain complex fused or bridged rings.

Facile synthesis of diverse o-iodoaryl triflates from o-silylaryl triflates by aluminum-mediated desilyliodination

A convenient method for preparing diverse o-iodoaryl triflates by the desilyliodination of o-silylaryl triflates has been developed. The treatment of o-silylaryl triflates with 1,3-diiodo- 5,5-dimethylhydantoin (DIH) in the presence of aluminum trichloride efficiently afforded the corresponding o-iodoaryl triflates, including those with multiple 1-iodo-2-(triflyloxy)arene moieties. Various multisubstituted o-iodoaryl triflates were easily prepared by the iridium-catalyzed CH borylation of readily available, simple o-silylaryl triflates, followed by deborylative transformations and subsequent desilyliodinaton.

Synthesis of diverse benzotriazoles from aryne precursors bearing an azido group via inter- and intramolecular cycloadditions

A diverse range of benzotriazoles were synthesized from various 3-(azidoalkoxy)aryne precursors, which were easily prepared by Mitsunobu etherification. Various bis-1,2,3-triazoles containing a benzotriazole skeleton were obtained via sequential azide-alkyne and azide-aryne cycloadditions. Intramolecular azido-aryne cycloaddition, conducted using the same starting materials, afforded new types of ring-fused benzotriazoles. In the latter case, the reaction proceeded efficiently even though the regioorientation of the azido group was the reverse of that usually observed in intermolecular reactions between 3-alkoxyarynes and an azide.