2016
DOI: 10.1002/ejoc.201600933
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ortho‐Lithiation Reactions of O‐(3,n‐Dihalophenyl) N,N‐Diethylcarbamates: Synthesis of Dihalosalicylamides and 2,3,n‐Trihalophenol Derivatives

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Cited by 10 publications
(12 citation statements)
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“…We planned to take advantage of the Truce reaction [26], more recently developed and expanded by Alemán and García-Ruano [27,28], involving the use of arylsulfonylacetylenes as alkynylating reagents for organolithium and organomagnesium compounds. Alemán and García Ruano established that [17,18].…”
Section: Synthesis Of O-o-alkynylaryl Carbamatesmentioning
confidence: 99%
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“…We planned to take advantage of the Truce reaction [26], more recently developed and expanded by Alemán and García-Ruano [27,28], involving the use of arylsulfonylacetylenes as alkynylating reagents for organolithium and organomagnesium compounds. Alemán and García Ruano established that [17,18].…”
Section: Synthesis Of O-o-alkynylaryl Carbamatesmentioning
confidence: 99%
“…In our case, we decided to revisit the reported conditions to use the starting carbamate as the limiting reagent. After some experimentation, we observed that only slight excess of the alkynylsulfone was required as the electrophilic partner for the organolithium intermediate 1a-Li generated from the regioselective ortho-lithiation of O-3-fluorophenyl N,N-diethylcarbamate 1a [17,18]. Under these conditions, the O-2-alkynyl-3-fluorophenyl carbamate 2aa could be isolated in good yield, referred to as the starting carbamate 1a (Scheme 2B).…”
Section: Synthesis Of O-o-alkynylaryl Carbamatesmentioning
confidence: 99%
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“…To synthesize N‐(pyridine‐2‐yl)isopropyl‐, N‐(2‐(4,5‐dihydrooxazol‐2‐yl)phenyl)‐ and N‐(quinolin‐8‐yl)amides of mono‐4‐, 5‐, 6‐fluorosalicylic acids, the Cu‐mediated dimerization and oxidative hydroxylation of C−H bond of the corresponding benzamides was used . Difluorosalicylamides have been synthesized from O‐difluorophenyl‐N,N‐diethylcarbamates by o‐lithiation and tandem transnitrilation/S N Ar reaction sequence …”
Section: Introductionmentioning
confidence: 99%