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Barton, Derek H. R.; Ozbalik, Nubar; Ramesh, M.

doi:10.1016/s0040-4020(01)81427-7

Cited by 124 publications

(37 citation statements)

References 23 publications

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“…1), which eventually leads to the formation of the homo-coupled product (5). 27,28) Bidentate phosphine ligands such as dppe and dppf were found to be inappropriate for this carbonylation (entries 11, 12). As expected, the yield of 4a was increased from 45 to 87% in the presence of PdCl 2 (PPh 3 ) 2 when the pressure of CO was raised from 1 to 20 atm.…”

Section: Resultsmentioning

confidence: 99%

Carbonylative Cross-Coupling Reaction of Ethynylstibane with Aryl Iodides

Kakusawa

Kurita

2006

CHEMICAL & PHARMACEUTICAL BULLETIN

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Recent remarkable development of novel transmetallating agents for cross-coupling reactions has been fascinating to many synthetic chemists because of its high reliability and wide applicability for C-C, C-O and C-N bond forming reaction.1,2) Especially, investigations on novel coupling agents involving typical heavier elements such as In, 3,4) Si, 5-7) Bi, 8,9) and Ge 10,11) attract much attention not only of heteroatom chemists, but also of synthetic chemists. These transmetallating agents can easily be activated and coupled with various organic halides under mild condition, based on a hypervalent strategy.12,13) One useful application of these transmetallating agents is carbonylative cross-coupling reaction which leads to the formation of unsymmetrical ketones in one-pot operation from an appropriate transmetallating agent and organic halides under carbon monoxide (CO) atmosphere. [14][15][16][17][18][19][20][21] The organoantimony(III) [Sb(III)] compounds are relatively stable and can be prepared easily compared to organoantimony(V) and hypervalent antimony compounds. The facile access of Sb(III) compounds stimulated us to employ them as practical organic reagents. We have recently explored the palladium-catalyzed cross-coupling reaction of Sb(III) compounds with organic halides and their versatile applicability, e.g. ethynylstibanes (1) were coupled with acyl chlorides, vinyl iodides and aryl iodides to give ethynylketones, 1,3-enynes, and arylacetylens, respectively. 22,23) We also demonstrated that these reactions were accelerated with microwave irradiation. 24) A mild and efficient Sb(III)-mediated cross-coupling reaction was also achieved with ethynyland ary-1,5-azastibocienes bearing an intramolecular N … Sb non-bonding interaction. 25,26) As an extension of the versatility of Sb(III) compounds as a transmetallating agent, we investigated the cross-coupling reaction of ethynylstibanes with aryl iodides under CO atmosphere. In the present reaction, the yield of the carbonylated coupling products is sensitive to the nature of the Pd catalyst, and superior results were obtained by using a monodentate phosphine-ligated Pd catalyst. It also appeared that a variety of unsymmetrical ethynyl ketones could be synthesized in excellent yield under high pressure condition (CO, 20 atm) even in the reactions with electron-deficient aryl iodides which usually gave inferior results due to their tendency to undergo decarbonylation. Results and DiscussionPd-Catalyzed Carbonylative Cross-Coupling Reaction of Ethynylstibane with Aryl Iodides under CO Atmosphere In order to optimize the reaction conditions, we initially attempted the reaction of ethynyldiphenylstibane (1) and iodobezene (2a) under atmospheric CO pressure using a variety of solvents in the presence of 5 mol% of various palladium (Pd) catalysts (Table 1). The reaction did not proceed in THF or benzene which was often employed for carbonylative cross-coupling with a variety of organometallic compounds.2,14-16,18,21) For direct cross-coupling reaction of 1 and...

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Section: Resultsmentioning

confidence: 99%

Carbonylative Cross-Coupling Reaction of Ethynylstibane with Aryl Iodides

Kakusawa

Kurita

2006

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…The low polarity of the C-Bi bond provides a moderate reactivity for this class of reagents, which thus allows the presence of numerous reactive or acidic functional groups on the electrophilic partner. Cross-coupling reactions involving triphenylbismuth was first reported by Barton et al in 1988. [17] Recently, the groups of Rao, [18] Tanaka, [19] and others [20] have extended the scope of this reaction to include other organobismuthanes.…”

Section: Introductionmentioning

confidence: 99%

“…Cross-coupling reactions involving triphenylbismuth was first reported by Barton et al in 1988. [17] Recently, the groups of Rao, [18] Tanaka, [19] and others [20] have extended the scope of this reaction to include other organobismuthanes. However, to the best of our knowledge, the full potential of organobismuthanes in the transfer of highly functionalized groups onto 2-halo(or 2-triflyl)azines and -diazines has never been demonstrated.…”

Section: Introductionmentioning

confidence: 99%

Palladium‐Catalyzed Cross‐Coupling Reaction of Functionalized Aryl‐ and Heteroarylbismuthanes with 2‐Halo(or 2‐Triflyl)azines and ‐diazines

Petiot

Gagnon

2013

Eur J Org Chem

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“…[1][2][3][4][5] As for the application of trivalent organoantimony compounds (stibanes), a wide variety of reactions such as self-coupling reactions, 6,7) cross-coupling reactions, [8][9][10][11][12][13] photoreaction, 14) and asymmetric reactions with optically active organoantimony compounds [15][16][17][18][19] have been reported during the last two decades. On the other hand, the conversion of benzoin into benzil has been accomplished by oxidation with a variety of reagents; i.e., bismuthane oxide, 20) bismuthane imides, 21) alumina-supported copper sulfate under microwave irradiation, 22) and the Burgess reagent, 23) and by transition metal-catalyzed oxidation with bismuth nitrate-copper acetate, 24) aerobic oxygen, 25,26) diacetoxyiodobenzene, 27) and allyl diethyl phosphate.…”

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confidence: 99%

Catalytic Action of Triarylstibanes: Oxidation of Benzoins into Benzyls Using Triarylstibanes Under an Aerobic Condition

Yasuike

Kishi²,

Kawara³

et al. 2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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Benzoins are simply oxidized to benzils in excellent yields with a catalytic amount of triarylstibanes under an aerobic condition. This catalytic oxidation is heteroatom-specific in the antimony compound and no reaction take place with other group 15 reagents such as triphenylphosphane, -arsane and -bismuthane. The reaction should involve an oxidation-reduction cycle between stibane Sb(III) and stiborane Sb(V) under air.

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Cited by 124 publications

References 23 publications

Carbonylative Cross-Coupling Reaction of Ethynylstibane with Aryl Iodides

Carbonylative Cross-Coupling Reaction of Ethynylstibane with Aryl Iodides

Palladium‐Catalyzed Cross‐Coupling Reaction of Functionalized Aryl‐ and Heteroarylbismuthanes with 2‐Halo(or 2‐Triflyl)azines and ‐diazines

Catalytic Action of Triarylstibanes: Oxidation of Benzoins into Benzyls Using Triarylstibanes Under an Aerobic Condition

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Untitled

Cited by 124 publications

References 23 publications

Carbonylative Cross-Coupling Reaction of Ethynylstibane with Aryl Iodides

Carbonylative Cross-Coupling Reaction of Ethynylstibane with Aryl Iodides

Palladium‐Catalyzed Cross‐Coupling Reaction of Functionalized Aryl‐ and Hetero­arylbismuthanes with 2‐Halo(or 2‐Triflyl)­azines and ‐diazines

Catalytic Action of Triarylstibanes: Oxidation of Benzoins into Benzyls Using Triarylstibanes Under an Aerobic Condition

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Palladium‐Catalyzed Cross‐Coupling Reaction of Functionalized Aryl‐ and Heteroarylbismuthanes with 2‐Halo(or 2‐Triflyl)azines and ‐diazines