Et3B-mediated two- and three-component coupling reactions via radical decarbonylation of α-alkoxyacyl tellurides: single-step construction of densely oxygenated carboskeletons† †Electronic supplementary information (ESI) available: Experimental protocols, characterization data, and NMR spectra of all new compounds. See DOI: 10.1039/c5sc00457h
نویسندگان
چکیده
The single-step construction of various densely oxygenated carboskeletons was achieved by radical-based twoand three-component coupling reactions of sugar derivatives, without the need for light or heat. Et3B/ O2-mediated decarbonylation readily converted a-alkoxyacyl tellurides to a-alkoxy carbon radicals, which intermolecularly added to glyoxylic oxime ether or enones to provide the two-component adducts. Furthermore, the three-component adducts were produced by an intermolecular aldol reaction between the aldehyde and the boron enolates generated by capture of the two-component radical intermediates by Et3B. This powerful coupling method serves as a novel strategy for the convergent synthesis of polyol natural products.
منابع مشابه
Triple aryne–tetrazine reaction enabling rapid access to a new class of polyaromatic heterocycles† †Electronic supplementary information (ESI) available: Experimental protocols, characterization data, X-ray crystallographic data (CIF) and NMR spectra of all new compounds. CCDC 1400529. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5sc01726b Click here for additional data file. Click here for additional data file.
متن کامل
Palladium-catalyzed cross-coupling of α-bromocarbonyls and allylic alcohols for the synthesis of α-aryl dicarbonyl compounds† †Electronic supplementary information (ESI) available. CCDC 1042318. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5sc00505a
The palladium-catalyzed coupling of olefins and organohalides is a versatile approach for synthesizing complex molecules from simple starting materials. We have developed a palladium-catalyzed coupling of α-bromocarbonyl compounds with allylic alcohols for the generation of acyclic aryl-substituted dicarbonyl compounds. The reaction proceeds via a tandem olefin insertion of an α-acyl radical fo...
متن کاملCopper-catalyzed direct alkylation of heteroarenes† †Electronic supplementary information (ESI) available: Experimental procedures, characterization and copies of 1H and 13C NMR spectra for all new compounds. See DOI: 10.1039/c6sc05622a Click here for additional data file.
متن کامل
Dual gold and photoredox catalysed C–H activation of arenes for aryl–aryl cross couplings† †Electronic supplementary information (ESI) available: Experimental procedures, full optimisation tables, control reaction, mechanistic studies, characterisation data and copies of NMR spectra of new compounds. See DOI: 10.1039/c6sc05469b Click here for additional data file.
A mild and fully catalytic aryl–aryl cross coupling via gold-catalysed C–H activation has been achieved by merging gold and photoredox catalysis. The procedure is free of stoichiometric oxidants and additives, which were previously required in gold-catalysed C–H activation reactions. Exploiting dual gold and photoredox catalysis confers regioselectivity via the crucial gold-catalysed C–H activa...
متن کاملRacemic hemiacetals as oxygen-centered pronucleophiles triggering cascade 1,4-addition/Michael reaction through dynamic kinetic resolution under iminium catalysis. Development and mechanistic insights† †Electronic supplementary information (ESI) available: Detailed experimental procedures and characterization of all new compounds, including copies of NMR spectra and HPLC chromatograms traces, computational details and Cartesian coordinates of all stationary points. CCDC 1525188 (4l), 1525189 (6a) and 1525190 (9a). For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7sc00009j Click here for additional data file. Click here for additional data file.
Department of Organic Chemistry II, Unive P.O. Box 644, 48080 Bilbao, Spain Departamento de Śıntesis y Estructura de Bi y Catálisis Homogénea (ISQCH), Universida Servicio de Resonancia Magnética Nuclear, C (CEQMA), Universidad de Zaragoza, CSIC, † Electronic supplementary information procedures and characterization of all NMR spectra and HPLC chromatogram Cartesian coordinates of all stationary...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
دوره 6 شماره
صفحات -
تاریخ انتشار 2015