“…The analytical data is in accordance with literature data. [5] ( 9, 143.2, 136.6, 135.0, 134.5, 122.3, 92.8. FTIR (ATR, neat) = 3079, 1702, 1668, 1459, 1294, 1248, 1096, 1015.…”
Section: Primary Benzyl Alcoholsmentioning
confidence: 99%
“…An important subclass of HVIs are diaryl- 3 -iodanes or diaryliodonium salts (DIS, 1, Figure 1). [5] Bearing iodobenzene as potent leaving group (hypernucleofug) [6] they have become frequently utilized reagents in a plethora of C(sp n )-H and Het-H arylation reactions. [7] Despite their outstanding performance as electrophilic group transfer reagents in transition metal-mediated and metal-free arylations their time-consuming multi-step synthesis often impedes their application.…”
Two one-pot procedures for the construction of carbon-bridged diaryliodonium triflates and tetrafluoroborates are described. Strong Brønsted acids enable the effective Friedel− Crafts alkylation with diversely substituted o-iodobenzyl alcohol derivatives, providing diphenylmethane scaffolds, which are subsequently oxidized and cyclized to the corresponding dibenzo-[b,e]iodininium salts. Based on NMR investigations and density functional theory (DFT) calculations, we could verify the so-farundescribed existence of two stable isomers in cyclic iodonium salts substituted with aliphatic side chains in the carbon bridge. Article pubs.acs.org/joc
“…The analytical data is in accordance with literature data. [5] ( 9, 143.2, 136.6, 135.0, 134.5, 122.3, 92.8. FTIR (ATR, neat) = 3079, 1702, 1668, 1459, 1294, 1248, 1096, 1015.…”
Section: Primary Benzyl Alcoholsmentioning
confidence: 99%
“…An important subclass of HVIs are diaryl- 3 -iodanes or diaryliodonium salts (DIS, 1, Figure 1). [5] Bearing iodobenzene as potent leaving group (hypernucleofug) [6] they have become frequently utilized reagents in a plethora of C(sp n )-H and Het-H arylation reactions. [7] Despite their outstanding performance as electrophilic group transfer reagents in transition metal-mediated and metal-free arylations their time-consuming multi-step synthesis often impedes their application.…”
Two one-pot procedures for the construction of carbon-bridged diaryliodonium triflates and tetrafluoroborates are described. Strong Brønsted acids enable the effective Friedel− Crafts alkylation with diversely substituted o-iodobenzyl alcohol derivatives, providing diphenylmethane scaffolds, which are subsequently oxidized and cyclized to the corresponding dibenzo-[b,e]iodininium salts. Based on NMR investigations and density functional theory (DFT) calculations, we could verify the so-farundescribed existence of two stable isomers in cyclic iodonium salts substituted with aliphatic side chains in the carbon bridge. Article pubs.acs.org/joc
“…15 A regioisomeric mixture of spiroacetals 11 and 12 was obtained independently of the catalytic system used. Formation of this mixture is easily explained considering that the reaction proceeds through the initial coordination of the gold complex to the alkyne.…”
Section: Asymmetric Spiroacetalizations Catalyzed By Chiral Phosphorimentioning
This perspective article briefly outlines the very few and recent methods reported in the literature on catalytic asymmetric synthesis of spiroacetals from achiral substrates.
“…An asymmetric gold-catalyzed dihydroalkoxylation of alkynes for the synthesis of benzannulated spiroacetals has been investigated in the presence of several phosphine ligands. The association of MeOBIPHEP ligand with the chiral silver salt AgTRIP led to the best results (eq 78) 104. …”
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