2019
DOI: 10.6023/cjoc201903037
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Chlorination of Anilide by Pd(OAc)2/N-Chloro-N-fluorobenzene- sulfonylamide

Abstract: A mild method for palladium-catalyzed halogenation of acetanilide with N-chloro-N-fluorobenzenesulfonylamide (CFBSA) as a chlorinating reagent, oxidant, and novel promoting reagent was achieved. The decomposition of byproduct N-fluoroben-zenesulfonylamine in the presence of Pd(OAc) 2 could accelerate the process of chlorination. Preliminary mechanism investigation showed that Pd catalyzed anilide directed C-H activation lead to the ortho chlorination selectivity. A series of ortho-chlorinated anilides were obt… Show more

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Cited by 3 publications
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“…[15] Recently, Yang reported a Pdcatalyzed halogenation of acetanilide with N-chloro-N-fluorobenzenesulfonylamide (CFBSA) to the preparation of o-chloroanilines (Scheme 2, a, iii). [16] However, despite these advances, CÀ H chlorination frequently required for transition metal catalysts or oxidants. Consequently, exploring an alternative protocol to the construction of functionalized chlorine-containing molecules is still high desirable.…”
Section: Introductionmentioning
confidence: 99%
See 1 more Smart Citation
“…[15] Recently, Yang reported a Pdcatalyzed halogenation of acetanilide with N-chloro-N-fluorobenzenesulfonylamide (CFBSA) to the preparation of o-chloroanilines (Scheme 2, a, iii). [16] However, despite these advances, CÀ H chlorination frequently required for transition metal catalysts or oxidants. Consequently, exploring an alternative protocol to the construction of functionalized chlorine-containing molecules is still high desirable.…”
Section: Introductionmentioning
confidence: 99%
“…In the past few years, Zheng and Bandi described an unexpected nucleophilic chlorination of quinone monoketals to the synthesis of o ‐chlorophenols or m ‐chlorophenols, respectively (Scheme 2, a, i and ii) [15] . Recently, Yang reported a Pd‐catalyzed halogenation of acetanilide with N ‐chloro‐ N ‐fluorobenzenesulfonylamide (CFBSA) to the preparation of o ‐chloroanilines (Scheme 2, a, iii) [16] . However, despite these advances, C−H chlorination frequently required for transition metal catalysts or oxidants.…”
Section: Introductionmentioning
confidence: 99%