Synthesis of 2,3-Diarylquinone by Palladium Catalyzed Cross-Coupling of Dibromoquinones with Heteroarylstannanes

Yoshida, Seigo; Kubo, Hiroaki; Saika, Tetsuyuki; Katsumura, Shigeo

doi:10.1246/cl.1996.139

Cited by 39 publications

(13 citation statements)

References 8 publications

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“…Single and double coupling reactions involving stannylthiophenes (and -pyrroles) with dibromoquinones have been reported [88]; another less conventional substrate used was a 2,6-dibromophosphosphabenzene (Scheme 4-30; here also single and double couplings were reported, as was the coupling of a 2-stannyl-pyridine) [89].…”

Section: Scheme 4-29mentioning

confidence: 97%

Organotin Reagents in Cross‐Coupling

Mitchell¹

1998

Metal‐Catalyzed Cross‐Coupling Reactions

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Organotin compounds offer many advantages for cross-coupling reaction, and it is thus not surprising that the palladium-catalyzed procedure introduced and developed by the late John Stille was seized upon by preparative organic chemists and used to great advantage for synthetic elaborations. Stille himself reviewed the area in 1986 [ 111, but his untimely death in July 1989 cut short his own work on the reaction which now bears his name. The present author attempted to cover the progress of the "Stille reaction" over the period 1986-mid-1991 in a review published in 1992 [2], and the publication of this monograph provides an opportunity to take another critical look at the applications of the procedure.In the early days various palladium catalyts were used, Pd(PPh,), and PhCH,PdCI(PPh,), being the two which were most frequently applied. A considerable amount of work has since gone into catalyst refinement, and here the name of V. Farina must be mentioned; he has published a number of important papers, and also reviewed his work and that of others [3]. Readers who wish to keep themselves up to date in this area in the future must hope that L. S. Hegedus will "keep up the good work' and continue to publish his invaluable annual surveys on the use of transition metals in organic synthesis [4] which always contain a section on tin compounds.Though strictly speaking outside the scope of this chapter, some brief details of other palladium-catalyzed reactions of organotin compounds (ditins and tin hydrides) will be given, as these can provide potentially useful reagents for Stille reactions. Many transition metals have found their niche in organic synthesis, but as far as reactions of organotins are concerned only palladium has been used to a large extent. However, relevant reactions of two other transition metals, copper and nickel, will be referred to at the end of this survey.One of the beauties of the Stille procedure is that various organic residues (alkyl, aryl, vinyl, alkynyl, etc.) can be transferred from tin to carbon in cross-couplings; although papers still continue to appear which deal with the transfer of more than one type of residue, "dedicated" papers whose goal is a particular type of elaboration are more common, and indeed there is a type of "hit list" reflecting the popularity of certain groups. Alkenyltins are by far the most important on this list, and we shall start by discussing their use; subsequent sections will mirror the range of application of other types of organotin. Stille Coupling of AlkenyltinsAlkenyltins can undergo coupling with a wide variety of organic halides and triflates and with acid chlorides. Although most of the examples reported deal with intermolecular coupling, intramolecular coupling is finding increasing favor, particularly as a step in 167 Metal-catalyzed Cross-coupling Reactions Edited by François Diederich, Peter J. Stang 4 Orgunotin Reqents in Cross-couplingnatural-product synthesis. The presence of two stannyl groups on the ethene unit offers synthetic advantages...

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Section: Scheme 4-29mentioning

confidence: 97%

Organotin Reagents in Cross‐Coupling

Mitchell¹

1998

Metal‐Catalyzed Cross‐Coupling Reactions

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“…The reaction between organotin compounds and various electrophiles takes place under neutral conditions in the presence of catalytic amounts of palladium [24] and has a high degree of selectivity. Both symmetricaly [25,26] and unsymmetrically substituted quinones [26] can be obtained by this method. The usual catalyst is Pd(PPh 3 ) 4 .…”

Section: Reactions Of Haloquinones With Heteroarylstannanes Catalymentioning

confidence: 99%

“…of tributylstannylheteroarene with yields of ~70%. Diheteroarylbenzoquinones 3 with various substituents at positions 2 and 3 are produced according to the following scheme [25,26]: In the reaction of 2,5-dibromobenzoquinone with an excess of 3-indolylstannane under the standard conditions for the Stille reaction the monosubstituted product is formed initially, and the 2,5-disubstituted benzoquinone 4 is then formed more slowly [27]. By this two-stage method it is possible to obtain 2,5-bisindolylquinones with various alkyl substituents at the nitrogen atom.…”

Section: Reactions Of Haloquinones With Heteroarylstannanes Catalymentioning

confidence: 99%

Methods for the Synthesis of Heteroaryl-substituted 1,4-Benzo- and 1,4-Naphthoquinones. (Review)

Batenko¹,

Karlivans²,

Valters³

2005

Chem Heterocycl Compd

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Methods for the synthesis of heteroaryl-substituted 1,4-benzo-and 1,4-naphthoquinones with a C-C bond between the heterocycle and quinone fragments are reviewed.Benzoquinones and their derivatives are widely used in organic synthesis as synthons and reagents [1,2]. They are used as electron-accepting components for the production of charge-transfer complexes and radicalion salts [3,4]. Derivatives of benzoquinones, isolated from natural sources, are subunits in many biological processes, such as electron transport, the photosynthesis of plants, the coagulation of blood, and cell respiration [1, 2, 5]. Reviews have been published on the synthesis of hydroxyquinones [6] and 1,4-benzoquinones condensed with heterocycles [7,8], but methods for the synthesis of heteroaryl derivatives of 1,4-benzoquinones and 1,4-naphthoquinones where the fragments of the heterocycle and the quinone are linked by a C-C bond have not so far been reviewed. Heteroaryl-substituted benzoquinones have demonstrated anticancer [9-11], antifungal, and antibacterial characteristics [11] and antidiabetic activity [12]. The present review is devoted to the analysis and classification of methods for the production of these compounds. Methods for the synthesis of heteroaryl derivatives of quinones can be divided into three groups: The formation of a C-C bond between the quinone and the heterocycle, construction of the heterocycle on the basis of the quinone, and construction of the quinone on the basis of the heterocycle.

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“…More recently, Yoshida et al have published the palladium-catalysed cross couplings of aryl and heteroarylstannanes with 2,3-dibromo-1,4-quinones to give a number of 2,3-bisaryl-1,4-naphthoquinones. [3,4] Similarly, Stagliano et al have reported a three-step procedure for the preparation of 2,3-bisaryl-1,4-quinones involving palladium-catalysed cross couplings of arylstannanes with activated 1,4-naphthoquinones, [5] and they have recently exploited this methodology in the synthesis of conocurvone analogues. [6] We sought a simple one-step procedure to 2,3-bisaryl-1,4naphthoquinones from readily available starting materials, that would also be amenable to a wide range of functional groups, and would avoid the use of tin.…”

Section: Introductionmentioning

confidence: 99%

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Best¹,

Sims²,

Winslade³

2001

Aust. J. Chem.

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A Al ll l e en nq qu ui ir ri ie es s a an nd d m ma an nu us sc cr ri ip pt ts s s sh ho ou ul ld d b be e d di ir re ec ct te ed d t to o: :publishing research papers from all fields of chemical science, including synthesis, structure, new materials, macromolecules, supramolecular chemistry, biological chemistry, nanotechnology, surface chemistry, and analytical techniques. ).2-Chloro-1,4-naphthoquinones underwent palladium-catalysed cross coupling reactions with arylboronic acids to give the corresponding 2-aryl-1,4-naphthoquinones. Similarly, 2,3-dichloro-1,4-naphthoquinone underwent efficient cross coupling reactions with arylboronic acids to give mono or bis adducts. The required 2-chloro-1,4-naphthoquinones were conveniently prepared from the corresponding 2-hydroxy-1,4-naphthoquinones by treatment with oxalyl chloride.

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Synthesis of 2,3-Diarylquinone by Palladium Catalyzed Cross-Coupling of Dibromoquinones with Heteroarylstannanes

Abstract: The synthesis of various kinds of both symmetrical and asymmetrical diarylquinones has been realized by the palladium catalyzed cross-coupling of 2,3-dibromoquinones with tributylstannylheteroaromatics.

Cited by 39 publications

References 8 publications

Organotin Reagents in Cross‐Coupling

Organotin Reagents in Cross‐Coupling

Methods for the Synthesis of Heteroaryl-substituted 1,4-Benzo- and 1,4-Naphthoquinones. (Review)

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