Convenient and direct preparation of tertiary phosphines via nickel-catalysed cross-coupling

Ager, David J.; Laneman, Scott A.

doi:10.1039/a705106i

Cited by 96 publications

(44 citation statements)

References 14 publications

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“…15 These methods, however, have some drawbacks in industrialization, such as use of pyrophoric diphenylphosphine or moisture-sensitive chlorodiphenylphosphine.…”

Section: New Synthetic Methods Of Binap and Its Variantsmentioning

confidence: 99%

Recent Advances of BINAP Chemistry in the Industrial Aspects

Kumobayashi

Miura

Sayo

et al. 2001

Synlett

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“…15 These methods, however, have some drawbacks in industrialization, such as use of pyrophoric diphenylphosphine or moisture-sensitive chlorodiphenylphosphine.…”

Section: New Synthetic Methods Of Binap and Its Variantsmentioning

confidence: 99%

Recent Advances of BINAP Chemistry in the Industrial Aspects

Kumobayashi

Miura

Sayo

et al. 2001

Synlett

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“…Solvent screening revealed that 1,4-dioxane was best with 12% yield (entry 9), and inorganic base [21] such as Na 2 CO 3 , K 2 CO 3 and K 3 PO 4 increased the yields in that order (entries 9 -11). The bidentate phosphine, 1,2-bis(diphenylphosphino)-ethane (DPPE) [22] and 1,3-bis(diphenylphosphino)propane (DPPP) [23] were also inactive under anhydrous conditions (entries 12 and 13). In analogy with DPPF, the ferrocenyl phosphine ligand substituted with a bulky alkyl group, 1,1'-bis(diisopropylphosphino)ferrocene (D-i-PrPF) [24] improved the yield (entry 14).…”

Section: Suzuki-miyaura Coupling Under Anhydrous Conditionsmentioning

confidence: 97%

A Novel Practical Synthesis of C‐2‐Arylpurines

Itoh¹,

Sato²,

Mase³

2004

Adv Synth Catal

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Suzuki-Miyaura cross-coupling of halopurines with arylboronic acids would be one of the most efficient methods to synthesize C-2-arylpurines. However, as this approach implied some potential disadvantages, we needed to devise a more efficient process. Starting with 4-amino-2-chloro-5-nitropyrimidine, readily prepared from 5-nitrouracil, seemed to potentially obviate our concerns, and the applicability of the Suzuki-Miyaura coupling was examined in detail. Considerable competitive hydrolysis occurred simultaneously with the desired reaction under the aqueous conditions typically employed in the Suzuki-Miyaura protocol. Excellent yields were obtained with 1,1'-bis(di-tert-butylphosphino)ferrocene ( ¼ D-t-BPF) under anhydrous conditions. Tolerance of various arylboronic acids was also found. Subsequent reduction with H 2 /Pd-C of one of the coupling adducts, 4-amino-5-nitro-2-phenylpyrimidine, gave the diamine, which was further condensed with activated acid derivatives to afford a wide variety of the 2-phenylpurine derivatives in excellent yields.

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“…Aryldiphenylphosphine can be obtained through palladium-catalyzed couplings of triphenylphosphine with either aryltriflates [4] or aromatic bromides [5]. Some years ago, it was reported that nickel complexes NiCl 2 (dppe) [6] or NiCl 2 (PPh 3 ) 2 [7] are efficient catalysts for the synthesis of triarylphosphines through reductive coupling of aryl triflates with chlorodiphenylphosphine. In related approaches, it was shown in this laboratory that a the NiBr 2 (bpy) catalyzed cross-coupling can be achieved by an electrochemical way [8] or using a zinc-mediated reductive coupling between aryl halides and chlorodiphenylphosphine in heated NMP (N-methylpyrrolidin-2-one) [9].…”

mentioning

confidence: 99%