514826-78-9

Upstream product

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

Downstream Products

• 514826-79-0 3-hydroxy-2-iodophenol trifluoromethanesulfonate 
• 138719-99-0 2-iodo-3-methoxyphenol trifluoromethanesulfonate 
• 138720-02-2 3-benzyloxy-2-iodophenol trifluoromethanesulfonate 
• 1402160-68-2 C₁₁H₁₀F₃IO₄S 

Relevant academic research and scientific papers

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.

Arynes as Radical Acceptors: TEMPO-Mediated Cascades Comprising Addition, Cyclization, and Trapping

The application of arynes as radical acceptors is described. The stable radical TEMPO (2,2,6,6-tetramethyl piperidine 1-oxyl) is shown to add to various ortho-substituted benzynes generating the corresponding aryl radicals which engage in 5-exo or 6-endo cyclizations. The cyclized radicals are eventually trapped by TEMPO. The introduced method provides ready access to various dihydrobenzofurans, oxindoles, and sultones by a conceptually novel approach.

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.

Selective aryne formation via Grob fragmentation from the [2+2] cycloadducts of 3-triflyloxyarynes

A chemoselective ring-opening protocol of the formal [2+2] cycloadducts of 3-triflyloxyarynes was developed to generate 2,3-aryne intermediate via Grob fragmentation. A variety of 1,3-di- and 1, 2, 3-trisubstituted arenes could be readily accessed through this [2+2] cycloaddition-2,3-aryne formation sequence. The regioselectivity in these transformations originates from the steric repulsion of the aliphatic chain.

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.

Rhodium-catalyzed regioselective carboacylation of olefins: A C-C bond activation approach for accessing fused-ring systems

Cut and sew: A rhodium-catalyzed regioselective carboacylation reaction of benzocyclobutenones was developed (see scheme). Directed by the pendant olefins, the C1-C2 bond is selectively cleaved rather than the C1-C8 bond. Subsequent alkene insertion leads to complex fused-ring systems. This reaction provides facile access to natural-product-like polycyclic structures in a chemoselective and atom-economic fashion. Copyright

Facile access to versatile polyaromatic building blocks: Selectively protected benzocyclobutenedione derivatives via regioselective [2 + 2] cycloaddition of α-alkoxybenzyne and ketene silyl acetal

A facile, divergent access to highly oxygenated benzocyclobutene derivatives was developed via the regioselective [2 + 2] cycloaddition of α-alkoxybenzynes and ketene silyl acetals. The cycloadducts could be converted to selectively protected alkoxybenzocyclobutenediones, an attractive class of compounds for the synthesis of polyaromatic compounds. As one possible application, divergent access to a regioisomer pair of sulfonylphthalides for the Hauser approach to polyaromatic compounds is described.