TBAF-promoted carbanion mediated sulfonamide cyclization of CF3-substituted N-allenamides an access to fluorinated gamma-sultams
نویسندگان
چکیده
γ-Sultams bearing a trifluorinated ethyl- or an ene- gem -difluorinated tether were obtained from CF 3 -substituted N -allenamides; experimental and DFT calculations suggested that this transformation involves 5- endo-dig cyclization on the ene-ynamide generated in situ .
منابع مشابه
Phosphine-catalyzed asymmetric additions of malonate esters to {gamma}-substituted allenoates and allenamides.
Because carbonyl groups are ubiquitous in organic chemistry, the ability to synthesize functionalized carbonyl compounds, particularly enantioselectively, is an important objective. We have developed a straightforward and versatile method for catalytic asymmetric carbon-carbon bond formation at the γ-position of carbonyl compounds, specifically, phosphine-catalyzed additions of malonate esters ...
متن کاملα-Haloarylsulfonamides: Multiple Cyclization Pathways to Skeletally Diverse Benzofused Sultams.
The development of new methods to skeletally diverse sultams based on a central α-halo benzene sulfonamide building block is reported. Several salient features of this building block are utilized in multiple reaction pathways, including the Heck reaction, C- and O-arylation, Sonogashira-Pauson-Khand, Sonogashira-intramolecular hydroamination, lithiative cyclization and domino aza-Michael Heck f...
متن کاملA highly efficient TBAF-promoted intramolecular cyclization of gem-dibromoolefins for the synthesis of 2-bromobenzofurans(thiophenes).
A highly efficient tetra-(n-butyl)ammonium fluoride (TBAF)-promoted intramolecular cyclization of gem-dibromoolefins has been developed for the synthesis of 2-bromobenzofused heterocycles. The reaction provides a convenient approach to 2-bromobenzofurans(thiophenes) from the corresponding readily available gem-dibromovinyl substrates without a metal.
متن کاملNucleophilic fluoroalkylation/cyclization route to fluorinated phthalides
Discribed in this article is a versatile and practical method for the synthesis of C3-perfluoroalkyl-substituted phthalides in a one-pot manner. Upon treatment of KF or triethylamine, 2-cyanobenzaldehyde reacted with (perfluoroalkyl)trimethylsilanes via nucleophilic addition and subsequent intramolecular cyclization to give perfluoroalkylphthalides in good yields.
متن کاملPyridine-promoted Cyclization of Functionalized N-Silylated Boron-Nitrogen Compounds
Dichloroboryldisilylamines [SiClm(CH3)3−m]N[Si(CH3)3](BCl2) (m = 1 – 3) as well as chloromethylboryl-bis-(chlorodimethylsilyl)amine [SiCl(CH3)2]2N[BCl(CH3)] form 1 : 1 adducts with pyridine (1 – 4). Those with m = 2 and 3 have been converted into functionalized diazadiboretidine derivatives which are still coordinated by pyridine: [(SiClm(CH3)3−m)NBCl · Py]2 (5: m = 2, 6: m = 3). Single-crystal...
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: Organic chemistry frontiers
سال: 2023
ISSN: ['2052-4110', '2052-4129']
DOI: https://doi.org/10.1039/d3qo00781b