A Combined Zirconocene Benzyne−Palladium Cross-Coupling Route to Substituted Biphenyls and Terphenyls

Frid, M. N.; Pérez, Dolores; Peat, and Andrew J.; Buchwald, Stephen L.

doi:10.1021/ja992345r

Cited by 38 publications

(14 citation statements)

References 19 publications

(13 reference statements)

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“…Buchwald has used an interesting method to produce bi-and terphenyl compounds. 20 A zirconium benzyne complex is generated in the usual manner, and then reacted with a palladium aryl species (Scheme 6). This inserts regioselectively into one of the zirconium-carbon bonds.…”

Section: Organozirconium-based Methodologymentioning

confidence: 99%

Applications of stoichiometric transition metal complexes in organic synthesis

Fletcher

Christie

2001

J. Chem. Soc., Perkin Trans. 1

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Introduction 2 Transition metal alkyl, alkenyl and allyl complexes in organic synthesis 2.1 Organozirconium-based methodology 2.2 Organotitanium-based methodology 2.3 Organoiron complexes 3 Group IV transition metal carbenes in organic synthesis 4 2 -Complexes in organic synthesis 5 3 -Complexes in organic synthesis 6 4 -Complexes in organic synthesis 7 5 -Complexes in organic synthesis 8 6 -Complexes in organic synthesis 9 Pauson-Khand reaction 10 References Scheme 1 Scheme 2

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Section: Organozirconium-based Methodologymentioning

confidence: 99%

Applications of stoichiometric transition metal complexes in organic synthesis

Fletcher

Christie

2001

J. Chem. Soc., Perkin Trans. 1

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“…This method provides a route into palladium-catalysed aryne coupling from the simple species Ar-M + Cp 2 Zr(Me)Cl, providing that Ar bears an ortho H for the thermolytic generation of methane in the resulting aryl methyl zirconocene. 127 Of course, due to the stability of the zirconocene complex, it is likely that the free aryne is not involved in the coupling.…”

Section: Scheme 53mentioning

confidence: 99%

Organometallic Generation and Capture of ortho-Arynes

Dyke¹,

Hester²,

Lloyd‐Jones³

2006

Synthesis

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This literature review focuses on the use of metal-or metalloid-based reagents to generate ortho-arynes from stable precursors via organometallic intermediates or to generate organometallic complexes of ortho-arynes. The review also encompasses the capture of arynes by organometallics to generate new complexes, with interesting reactivity in their own right, or as intermediates in catalytic systems. The purpose of the review is to highlight the novelty, utility and versatility of the interaction of organometallic species with arynes and their precursors. These points are illustrated through a number of examples of the application of such methods in the preparation of complex organic molecules. The review contains some 197 references and covers the literature up to May 2006.

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“…For example, transmetallation of zirconocenearyne complex 26 with the palladium complex generated from Pd(0) and mbromo(trifluoromethyl)benzene regioselectively affords palladium(II) complex 27, which after reductive elimination can be iodinated to 28 [22].Alternatively, treatment of 26 with B(OEt) 3 results in the formation of 29, and its iodination and oxidation leads to 30 [23]. …”

Section: Aryne Complexes Of Early Transition Metalsmentioning

confidence: 99%