Highly regioselective tandem formal substitution and decarboxylation of 2-acyl-1-chlorocyclopropanecarboxylates with sodium sulfinates
نویسندگان
چکیده
منابع مشابه
Palladium-catalyzed tandem reaction of 2-hydroxyarylacetonitriles with sodium sulfinates: one-pot synthesis of 2-arylbenzofurans.
The first example of the palladium-catalyzed one-pot synthesis of 2-arylbenzofurans in moderate to excellent yields via a tandem reaction of 2-hydroxyarylacetonitriles with sodium sulfinates is reported. A plausible mechanism for the formation of 2-arylbenzofurans involving desulfinative addition and intramolecular annulation reactions is proposed. Moreover, the present synthetic route to benzo...
متن کاملFormation and aromatization of strained bicyclic pyrazolidines via tandem reaction of alkyl 2-aroyl-1-chlorocyclopropanecarboxylates with acylhydrazones.
A base-promoted reaction between alkyl 2-aroyl-1-chlorocyclopropanecarboxylates and acylhydrazones is described. In common solvents, the reactions proceed smoothly under mild conditions, providing mainly the formal substitution product , as well as a little amount of the formal [3 + 2] cycloaddition product . This strained bicyclic pyrazolidine , however, became the predominant product in DMSO....
متن کاملPalladium-catalyzed desulfitative hydroarylation of alkynes with sodium sulfinates.
A palladium-catalyzed desulfitative hydroarylation of alkynes with aryl sulfinic acid sodium salts is described. The reaction showed good regio- and stereoselectivity, and afforded the hydroarylation products in good yields. Various functional groups were well tolerated under the optimized reaction conditions.
متن کاملIntramolecular homolytic substitution of sulfinates and sulfinamides--a computational study.
Ab initio and density functional theory (DFT) calculations predict that intramolecular homolytic substitution by alkyl radicals at the sulfur atom in sulfinates proceeds through a smooth transition state in which the attacking and leaving radicals adopt a near collinear arrangement. When forming a five-membered ring and the leaving radical is methyl, G3(MP2)-RAD//ROBHandHLYP/6-311++G(d,p) calcu...
متن کاملPlatinum-catalyzed tandem cycloisomerization reaction of benzoendiynyl esters: regioselective long-range 1,5-acyl migration.
A Pt(II)-catalyzed intramolecular chemo- and regioselective pentannulation/long-range 1,5-acyl migration reaction is described. This cascade cycloisomerization protocol produces a wide variety of benzofulvene diketones in good to excellent yields with exclusively the Z configuration of the exocyclic double bond of the final product. The (18)O isotope experiment together with (13)C NMR, HRMS, an...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
ژورنال
عنوان ژورنال: Tetrahedron
سال: 2016
ISSN: 0040-4020
DOI: 10.1016/j.tet.2016.04.062