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Volumn 132, Issue 34, 2010, Pages 11978-11987

Scope and mechanism of allylic C-H amination of terminal alkenes by the palladium/PhI(OPiv)2 catalyst system: Insights into the effect of naphthoquinone

Author keywords

[No Author keywords available]

Indexed keywords

C-H OXIDATIVE; CATALYST SYSTEM; CH-BOND ACTIVATION; FUNCTIONALIZATIONS; LIMITING STEP; NAPHTHOQUINONE; PALLADIUM CATALYST; RE-OXIDATION; STRONG OXIDANTS; SYSTEMATIC ANALYSIS; TERMINAL ALKENES; UNACTIVATED OLEFINS;

EID: 77956083490     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja1030936     Document Type: Article
Times cited : (197)

References (125)
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    • For recent examples for Pd-catalyzed oxidative amination of alkenes, see
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    • There are a lot of palladium black observed in the reaction eq 1.
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    • In our previous studies, (8c) although the reaction afforded the allylic C-H amination product with very low yield (< 10%), the alkenes isomerization was inhibited when a stoichometric amount of base (NaOAc) was used
    • In our previous studies, (8c) although the reaction afforded the allylic C-H amination product with very low yield (< 10%), the alkenes isomerization was inhibited when a stoichometric amount of base (NaOAc) was used.
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    • 1,4-Naphthoquinone has been used as oxidant in palladium-catalyzed alcohol oxidation, see
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    • For some examples on the palladium-catalyzed amination of alkenes with N -tosylcarbamate as nitrogen nucleophile, which were proposed to go through trans -aminopalladation pathway, see ref 9a and
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    • For the transformation via Pd(0/II) mechanism, White and coworker have reported that the reaction of allylic acetate with 2a afforded the allylic amination product and isomer of allylic acetate, which involved an oxidative addition of Pd(0), see the Supporting Information of ref 8b
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    • The formation of 25 is raised from PhI and 3a catalyzed by Pd catalyst, see the Supporting Information for details.
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    • II is also well-precedented, see ref 31 and
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    • The similar kinetic isotope effect (KIE = 2.2) was obtained in the allylic alkylation with BQ as oxidant, see
    • The similar kinetic isotope effect (KIE = 2.2) was obtained in the allylic alkylation with BQ as oxidant, see
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    • The rate determining pre-equilibrium step is quite rare in the literature, see
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    • 2 was keep in the same concentration, the HX concentration should be a constant.
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    • 2. For details, see
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    • II(BQ) complex is extremely rare in the literature, and its isolation has remained unsuccessful, the relative study cannot currently be conducted by experiments. For the theoretical studies on allylPd(II)-BQ complexes by computational calculation, see
    • II(BQ) complex is extremely rare in the literature, and its isolation has remained unsuccessful, the relative study cannot currently be conducted by experiments. For the theoretical studies on allylPd(II)-BQ complexes by computational calculation, see
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    • The allyl-Pd(IV) complexes have been reported from the reaction of stable Pd(II) cycle with allyl bromide, see
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.