Dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium(II): an effective catalyst for cross-coupling of secondary and primary alkyl Grignard and alkylzinc reagents with organic halides

Hayashi, Tamio; Konishi, Mitsuo; Kobori, Yuji; Kumada, Makoto; Higuchi, Taiichi; Hirotsu, Ken

doi:10.1021/ja00313a032

Cited by 764 publications

(368 citation statements)

References 5 publications

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“…The angle between the cyclopentadienyl rings is 3.25 °, as compared with 6.2 ° in [PdC12(dppf)] or [NiBr2(dppf)] (Butler, Cullen, Kim, Rettig & Trotter, 1985). The P(1)...P(2) distance is 3.583 (4) A which lies within the previously reported range [3.45-3.78A (Hayashi, Konishi, Kobori, Kumada, Higuchi & Hirotsu, 1984)]. The distances between the Fe atom and the cyclopentadienyl rings (1.630-1.640A) are also within normal ranges (Fair, 1990).…”

Section: Actasupporting

confidence: 78%

Structure of an iridium complex of 1,1'-bisdiphenylphosphinoferrocene

Bedford¹,

Chaloner²,

Hitchcock³

1993

Acta Crystallogr C

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Section: Actasupporting

confidence: 78%

Structure of an iridium complex of 1,1'-bisdiphenylphosphinoferrocene

Bedford¹,

Chaloner²,

Hitchcock³

1993

Acta Crystallogr C

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“…This effect on the reductive elimination was also found by Hayashi [184] and van Leeuwen [185] in the palladium-catalyzed cross-coupling reaction of Grignard reagents with aryl halides.…”

Section: 14supporting

confidence: 76%

Mechanistic Aspects of Metal‐Catalyzed C—C and C—X Bond‐Forming Reactions

Echavarren

Cárdenas

2005

ChemInform

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Cross-coupling reactions, such as the Stille reaction of organostannanes [1][2][3] and the Suzuki (or Suzuki-Miyaura) cross-coupling of organoboron compounds [4] have settled amongst the more general and selective palladium-catalyzed cross-coupling reactions [5] (Scheme 1-1). These reactions are closely related to other cross-couplings based on transmetallations of a variety of hard or soft organometallic nucleophiles [6] such as the Hiyama [7,8], Sonogashira [9], Kumada (or Kumada-Corriu), and other related couplings [10][11][12].Coupling reactions are somewhat related to the Heck alkenylation of organic electrophiles [13, 14], which is often referred to in the literature as a coupling process. However, although the first steps in both processes are identical, in the Heck reaction there is no transmetallation step. In the alkenylation reaction, the C-C bond is formed by an insertion process, which is followed by a b-hydride elimination to form the substituted alkene product. Cross-coupling (transmetallationbased) processes are a family of closely related catalytic processes that share most mechanistic aspects, although some differences exist on the activation of the organometallic nucleophile. So far, most of the detailed mechanistic studies have cen-

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“…The conformations of the phenyl rings in the two complexes (illustrated best in Fig. 2 The palladium and platinum atoms adopt a distorted square planar geometry similar to that observed previously for other diphosphine palladium and platinum complexes [17,23]. P2 is significantly displaced from the MCl 2 plane by ca 0.3 Å, whereas P1 is approximately in the MCl 2 plane.…”

Section: X-ray Structural Analysessupporting

confidence: 73%

Four-coordinate complexes of bis(1-diphenylphosphinoindenyl)iron(II)

Adams

Curnow

Fern

2006

Inorganica Chimica Acta

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Palladium, platinum and rhodium complexes of racand meso-bis(1-diphenylphosphinoindenyl)iron(II) (1) are reported. Both rac and meso isomers of {bis(1-diphenylphosphinoindenyl)iron(II)}palladium dichloride (rac-and meso-2) were characterized by X-ray crystallography along with the rac isomer of the Pt analogue (rac-3). NMR analysis of thetetraphenylborate suggests a similar structure in solution. Coupling reactions of n-and sec-BuCl with bromobenzene in THF are catalysed by rac-2 and found to be similar to (PPh 3 ) 2 PdCl 2 but poorer than (dppf)PdCl 2 in diethyl ether.

show abstract

Dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium(II): an effective catalyst for cross-coupling of secondary and primary alkyl Grignard and alkylzinc reagents with organic halides

Cited by 764 publications

References 5 publications

Structure of an iridium complex of 1,1'-bisdiphenylphosphinoferrocene

Structure of an iridium complex of 1,1'-bisdiphenylphosphinoferrocene

Mechanistic Aspects of Metal‐Catalyzed C—C and C—X Bond‐Forming Reactions

Four-coordinate complexes of bis(1-diphenylphosphinoindenyl)iron(II)

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