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Issue 10, 2006
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Bis(2-diphenylphosphinoxynaphthalen-1-yl)methane: transition metal chemistry, Suzuki cross-coupling reactions and homogeneous hydrogenation of olefins

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Abstract

Transition metal complexes of bis(2-diphenylphosphinoxynaphthalen-1-yl)methane (1) are described. Bis(phosphinite) 1 reacts with Group 6 metal carbonyls, [Rh(CO)2Cl]2, anhydrous NiCl2, [Pd(C3H5)Cl]2/AgBF4 and Pt(COD)I2 to give the corresponding 10-membered chelate complexes 2, 3 and 5–8. Reaction of 1 with [Rh(COD)Cl]2 in the presence of AgBF4 affords a cationic complex, [Rh(COD){Ph2P(–OC10H6)(µ-CH2)(C10H6O–)PPh2PP}]BF4 (4). Treatment of 1 with AuCl(SMe2) gives mononuclear chelate complex, [(AuCl){Ph2P(–OC10H6)(µ-CH2)(C10H6O–)PPh2PP}] (9) as well as a binuclear complex, [Au(Cl){µ-Ph2P(–OC10H6)(µ-CH2)(C10H6O–)PPh2PP}AuCl] (10) with ligand 1 exhibiting both chelating and bridged bidentate modes of coordination respectively. The molecular structures of 2, 6, 7, 9 and 10 are determined by X-ray studies. The mixture of Pd(OAc)2 and 1 effectively catalyzes Suzuki cross-coupling reactions of a range of aryl halides with aryl boronic acid in MeOH at room temperature or at 60 °C, giving generally high yields even under low catalytic loads. The cationic rhodium(I) complex, [Rh(COD){Ph2P(–OC10H6)(µ-CH2)(C10H6O–)PPh2PP}]BF4 (4) catalyzes the hydrogenation of styrenes to afford the corresponding alkyl benzenes in THF at room temperature or at 70 °C with excellent turnover frequencies.

Graphical abstract: Bis(2-diphenylphosphinoxynaphthalen-1-yl)methane: transition metal chemistry, Suzuki cross-coupling reactions and homogeneous hydrogenation of olefins

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Publication details

The article was received on 25 Jul 2005, accepted on 31 Oct 2005 and first published on 23 Nov 2005


Article type: Paper
DOI: 10.1039/B510589G
Dalton Trans., 2006, 1322-1330

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    Bis(2-diphenylphosphinoxynaphthalen-1-yl)methane: transition metal chemistry, Suzuki cross-coupling reactions and homogeneous hydrogenation of olefins

    B. Punji, J. T. Mague and M. S. Balakrishna, Dalton Trans., 2006, 1322
    DOI: 10.1039/B510589G

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