Generation of diverse 2-pyrones via palladium-catalyzed site-selective Suzuki-Miyaura couplings of 3-bromo-4-tosyloxy-2-pyrone.
نویسندگان
چکیده
Based on different reactivity of the (pseudo)halide substituents in the 2-pyrone (3-Br and 4-OTs), palladium-catalyzed sequential site-selective Suzuki-Miyaura cross-coupling reactions of 3-bromo-6-methyl-4-tosyloxy-2-pyrone are described, which afford the diverse 2-pyrones in good yields.
منابع مشابه
Selectivity, Compatibility, Downstream Functionalization, and Silver Effect in the Gold and Palladium Dual-Catalytic Synthesis of Lactones
The chemo- and regioselectivity and functional group compatibility in gold and palladium cooperatively catalyzed cross-coupling reactions were determined in the synthesis of lactones; the selectivity in the gold and palladium dual-metal catalysis system was distinct from that available for the same class of substrates in systems with only gold catalysis or only palladium catalysis rather than d...
متن کاملDirect one-pot synthesis of primary 4-amino-2,3-diaryl-quinolines via Suzuki-Miyaura cross-coupling of 2-aryl-4-azido-3-iodoquinolines with arylboronic acids.
Palladium-catalyzed Suzuki-Miyaura cross-coupling of 2-aryl-4-azido-3-iodo-quinolines with arylboronic acids afforded the corresponding primary 4-amino-2,3-diarylquinolines in a single-pot operation along with symmetrical biaryls and traces of the 2,3-diaryl-4-azidoquinolines. A plausible mechanism, which implicates palladium hydride species in the reduction of the incipient 2,3-diaryl-4-azidoq...
متن کاملSelective synthesis of dibenzo[a,c]cyclooctatetraenes via palladium-catalyzed [4+4] cyclic homocoupling of borylvinyl iodobenzene derivatives.
Dibenzo[a,c]cyclooctatetraenes were selectively generated in good yields from the palladium-catalyzed [4+4] cyclic homocoupling of borylvinyl iodobenzene derivatives, which were prepared via the selective Suzuki-Miyaura cross-coupling of the gem-diboryl reagents with iodo compounds.
متن کاملOne-pot synthesis of 2,3,4-triarylquinolines via suzuki-miyaura cross-coupling of 2-aryl-4-chloro-3-iodoquinolines with arylboronic acids.
Palladium-catalyzed Suzuki cross-coupling of 2-aryl-4-chloro-3-iodoquinolines with excess arylboronic acids (2.5 equiv.) in the presence of tricyclohexylphosphine afforded the 2,3,4-triarylquinolines in one-pot operation. The incipient 2,3-diaryl-4-chloroquinolines were also prepared and transformed to the primary 4-amino-2,3-diarylquinolines and 2,3-diarylquinolin-4(1H)-ones.
متن کاملSynthesis of new styrylarenes via Suzuki-Miyaura coupling catalysed by highly active, well-defined palladium catalysts.
An efficient synthetic route for well-defined palladium(0) complexes [Pd(η(2)-dba)(PPh3)2] (2), [Pd(η(2)-dba)(PCy3)2] (3) and their crystallographic structures is reported. This is the first crystallographic characterization of palladium complexes coordinated with one dibenzylideneacetone and two phosphines. A highly effective, fully controlled method for selective synthesis of mono- (5-9) and ...
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:
- Organic & biomolecular chemistry
دوره 9 18 شماره
صفحات -
تاریخ انتشار 2011