Sequential In-catalyzed intramolecular hydroarylation and Pd-catalyzed cross-coupling reactions using bromopropargyl aryl ethers and amines†
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Indium-catalyzed intramolecular hydroarylation of aryl propargyl ethers.
Indium(III) halides catalyze efficiently the intramolecular hydroarylation (IMHA) of aryl propargyl ethers. The reaction proceeds regioselectively with terminal and internal alkynes bearing electron-rich and electron-deficient substituents in the benzenes and alkynes affording only the 6-endo dig cyclization product. Additionally, a sequential indium-catalyzed IMHA and palladium-catalyzed Sonog...
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[reaction: see text] A one-pot protocol for converting 1,3- and 1,4-substituted aryl halides to arylamine boronate esters is described. This is achieved by sequential Ir-catalyzed aromatic borylation at the least hindered C-H bond of the aryl halide and subsequent Pd-catalyzed C-N coupling at the halide position of the crude arylboronic ester.
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Pd-catalyzed cross-coupling of furfural tosylhydrazones with aryl halides produces 2-furylmethylenepalladium halides, which can undergo intramolecular nucleophilic dearomatization to provide spiroacetal enol ethers. This is the first report on the formation of 2-furylmethylenepalladium halides from stable furfural hydrazones instead of from 2-furylmethyl halides, which are not readily accessibl...
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An interesting sequential reaction involving Sonogashira coupling, propargyl-allenyl isomerization, intramolecular [4 + 2] cycloaddition, and bridged oxa-ring opening has been realized, providing a facile method for the synthesis of functionalized dihydroisobenzofurans from easily accessible starting materials with a decent diastereoselectivity.
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Palladium-catalyzed cross-coupling reactions of alpha-aryl-beta,beta-difluoroenol silyl and alpha-aryl-beta-fluoroenol silyl ethers with aryl bromides proceed smoothly with good functional compatibility.
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