Selective mono reduction of bisphosphine
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- Ὅμηρος Ζαφειρόπουλος
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1 Griffith Research Online Selective mono reduction of bisphosphine oxides under mild conditions Author etersson, Maria, Loughlin, Wendy, Jenkins, Ian ublished 2008 Journal Title Chemical Communications DOI Copyright Statement Copyright 2008 Royal Society of Chemistry. This is the author-manuscript version of the paper. Reproduced in accordance with the copyright policy of the publisher. lease refer to the journal link for access to the definitive, published version. Downloaded from Link to published version
2 S1 Selective Mono reduction of bis-phoshine oxides under mild conditions Maria J. etersson, a Wendy A. Loughlin b and Ian D. Jenkins,* a a Eskitis Institute, Griffith University, Nathan, Brisbane, QLD, 4111, Australia. I.Jenkins@griffith.edu.au; b Eskitis Institute and School of Biomolecular and ysical Sciences, Griffith University, Nathan, Brisbane, QLD, 4111, Australia. Supporting Information 1. Oxidation of bis-phosphines. S H NMR and 31 NMR spectra and for Bis(diphenylphosphino)methane monoxide s4 1,2-bis(diphenylphosphino)ethane monoxide S5 1,3-Bis(diphenylphosphino)propane monoxide.....s6 1,4-Bis(diphenylphosphino)butane monoxide..s7 (±)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl monooxide..s8 (S)-2,2'-Bis[di(p-tolyl)phosphino]-1,1'-binaphthyl monooxide......s Mass Spectral and 1 H NMR data for Bis(diphenylphosphino)methane monoxide.....s11 1,2-bis(diphenylphosphino)ethane monoxide S11 1,3-Bis(diphenylphosphino)propane monoxide s11 1,4-Bis(diphenylphosphino)butane monoxide......s11 (±)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl monooxide. S11 (S)-2,2'-Bis[di(p-tolyl)phosphino]-1,1'-binaphthyl monooxide..s11
3 1. Oxidation of bis-phosphines S2 Representative example: 1,2-Bis(diphenylphosphinyl)ethane (1): 1,2-Bis-(diphenyl phosphino)ethane (5.0 g, 12.6 mmol) was dissolved in DCM (500 ml) and the solution shaken in a separating funnel with hydrogen peroxide (50 ml, 30% wt-% solution in water). The completion of the reaction (approx. 5 min) was determined by TLC (100% DCM). The DCM layer was washed with water (2 x 500 ml), dried (anhydrous MgSO 4 ), and filtered. The solvent was removed to afford a white solid. Recrystallisation (methanol/ethyl acetate) of the solid gave 1,2- bis(diphenylphosphinyl)ethane 1 as an amorphous white solid (5.35 g, 99%). Mp ºC (lit., 1 mp ºC). δ H (400 MHz, CDCl 3 ) 2.55 (4H, br d, J = 2.4 Hz), 7.45 (8H, dd, J = 7.1, 7.1 Hz), 7.51 (4H, dd, J = 7.1, 7.1 Hz), (8H, m); δ (162 MHz, CDCl 3 ) 31.6 (s, 2). MS (ESI) m/z ([M+H] +, 64%), ([M+Na] +, 100%). Additional phosphine oxides were prepared. Bis(diphenylphosphinyl)methane: (1.01g, 93%). Mp o C (lit., 1 mp o C). δ H (400 MHz, CDCl 3 ) 3.56 (2H, br t, J = 14.6 Hz), (8H, m), 7.43 (4H, dd, J = 7.4, 7.4 Hz), (8H, m); δ (162 MHz, CDCl 3 ) δ 26.4 (s, 2). MS (ESI) m/z ([M+H] +, 85%), ([M+Na] +, 100%). 1,3-Bis(diphenylphosphinyl)propane: (1.04 g, 97%). Mp o C (lit., 1 mp o C). δ H (400 MHz, CDCl 3 ) (2H, m), (4H, m), (8H, m), (4H, m), (8H, m); δ (162 MHz, CDCl 3 ) δ 32.6 (s, 2). MS (ESI) m/z ([M+H] +, 37%), ([M+Na] +, 100%). 1,4-Bis(diphenylphosphinyl)butane: (1.02g, 95%). Mp o C (lit., 1 mp o C). δ H (400 MHz, CDCl 3 ) (4H, m), (4H, m), (8H, m), (4H, m), (8H, m); δ (162 MHz, CDCl 3 ) δ 34.1 (s, 2). MS (ESI) m/z ([M+H] +, 86%), ([M+Na] +, 100%). rac-2,2 -Bis(diphenylphosphinyl)-1,1 -binaphthyl: (2.06 g, 98%). Mp ºC (lit., 2 mp ºC). δ H (400 MHz, CDCl 3 ) (4H, m), (10H, m), (10H, m), 7.71 (4H, br dd, J = 7.9, 12.3 Hz), 7.82 (2H, br d, J = 7.9 Hz), 7.86 (2H, dd, J = 2.4, 7.9 Hz) ; δ (162 MHz, CDCl 3 ) 30.6 (s, 2). MS (ESI) m/z ([M+H] +, 100%), ([M+Na] +, 26%).
4 S3 (S)-2,2 -Bis(di-p-tolylphosphinyl)-1,1 -binaphthyl: (299 mg, 97%). Mp ºC (lit., 2 mp ºC). δ H (400 MHz, CDCl 3 ) 2.31 (12H, d, J = 15.6 Hz), (4H, m), (8H, m), (4H, m), (8H, m), (4H, m); δ (162 MHz, CDCl 3 ) 30.6 (s, 2). MS (ESI) m/z ([M+H] +, 100%), ([M+Na] +, 24%), ([M+Li] +, 100%). HRMS calcd for C 48 H 39 O 2 2 [M-H] - : Found: References: 1 Dictionary of Organophosphorus Compounds (Ed. R. S. Edmundson) 1988, (Chapman and Hall: London). 2 H. Takaya, K. Mashima, K. Koyano, M. Yagi, H. Kumobayashi, T. Taketomi, S. Akutagawa, R. Noyori, Journal of Organic Chemistry 1986, 51,
5 S H NMR and 31 NMR spectra O 1 H NMR at 400MHz in CDCl 3 31 NMR at 162MHz in CDCl 3
6 S5 O 1 H NMR at 400MHz in CDCl NMR at 162MHz in CDCl 3
7 S6 O 1 H NMR at 400MHz in CDCl 3 31 NMR at 162MHz in CDCl 3
8 S7 O 1 H NMR at 400MHz in CDCl 3 31 NMR at 162MHz in CDCl 3
9 O S H NMR at 400MHz in CDCl 3 31 NMR at 162MHz in CDCl 3
10 O S9 Tol 2 1 H NMR at 400MHz in CDCl 3 Tol 2 31 NMR at 162MHz in CDCl 3
11 13 C NMR at 100MHz in CDCl 3 S10
12 3. Mass Spectral and 1 H NMR data for S11 Bis(diphenylphosphino)methane monoxide δ H (400 MHz, CDCl 3 ) 3.11 (2H, br d, J = 12.8 Hz), (6H, m), (8H, m), (2H, m), (4H, m). MS (ESI) m/z ([M+H] +, 100%). 1,2-Bis(diphenylphosphino)ethane monoxide (2) δ H (400 MHz, CDCl 3 ) 2.30 (4H, br s), (10H, m), (4H, m), (2H, m), (4H, m). MS (ESI) m/z ([M+H] +, 100%), ([M+Li] +, 100%). 1,3-Bis(diphenylphosphino)propane monoxide δ H (400 MHz, CDCl 3 ) (2H, m), 2.17 (2H, br t, J = 7.6 Hz), (2H, m), (6H, m), (4H, m), (4H, m), (2H, m), (4H, m). MS (ESI) m/z ([M+H] +, 100%). 1,4-Bis(diphenylphosphino)butane monoxide δ H (400 MHz, CDCl 3 ) (2H, m), (2H, m), (2H, m), (2H, m), (6H, m), (4H, m), (6H, m), (4H, m). MS (ESI) m/z ([M+H] +, 100%). 2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl monooxide δ H (400 MHz, CDCl 3 ) 6.65 (1H, br d, J = 8.4 Hz), (1H, m), 6.82 (1H, br d, J = 8.4 Hz), (21H, series of m), 7.42 (1H, dd, J = 3.2, 8.4 Hz), 7.61 (3H, dd, J = 8.6, 11.8 Hz), 7.70 (1H, d, J = 8.0 Hz), 7.75 (1H, d, J = 8.6 Hz), 7.82 (1H, d, J = 8.0 Hz), 7.91 (1H, br dd, J = 2.4, 8.6 Hz). MS (ESI) m/z ([M+H] +, 100%). 2,2'-Bis(ditolylphosphino)-1,1'-binaphthyl monooxide δ H (400 MHz, CDCl 3 ) 2.25 (6H, br s), 2.29 (6H, br d, J = 12 Hz), 6.64 (1H, br d, J = 8.4 Hz), 6.75 (1H, br dd, J = 7.6, 7.6 Hz), (12H, series of m), 7.20 (2H, dd, J = 7.6, 7.6 Hz), (4H, m), (3H, m), 7.71 (3H, br dd, J = 8.5, 13.6 Hz), 7.82 (1H, br d, J = 8.5 Hz), 7.93 (1H, br dd, J = 8.6, 8.8 Hz). MS (ESI) m/z ([M+H] +, 100%). Anal. Calcd for C 48 H 40 O 2 : C, 82.98; H, Found: C, 82.65; H, 6.01.
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