Suzuki-Miyaura Coupling of NHC-Boranes: a New Addition to the C-C Coupling Toolbox
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1 Supporting Information Suzuki-Miyaura Coupling of HC-Boranes: a ew Addition to the C-C Coupling Toolbox Julien Monot, a Malika Makhlouf Brahmi, a Shau-Hua Ueng, a Carine Robert, a Marine Desage-El Murr, a Dennis P. Curran,*,a,b Max Malacria,*,a Louis Fensterbank,*,a and Emmanuel Lacôte*,a. a Institut Parisien de chimie moléculaire (UMR CRS 71), C. 229, UPMC Univ Paris 06, 4 place Jussieu, Paris, France. b University of Pittsburgh, Department of Chemistry,Pittsburgh, PA 152, USA. General Remarks. Reactions were carried out under argon gas, with magnetic stirring and redistilled solvents when necessary. Thin layer chromatography (TLC) was performed on Merck F254 silica gel Merck Geduran SI A silica gel (35 70 mm) was used for column chromatography. The melting points reported were measured with a SMP3 Stuart Scientific melting point apparatus and were uncorrected. IR spectra were recorded with a Bruker Tensor 27 ATR diamant PIKE spectrometer. 1 H-, 13 C- and 11 B-MR spectra were recorded with Bruker Avance 0 spectrometer fitted with a BBF probe 13 C/ 11 B/ 1 H including z gradient. Chemical shifts are given in ppm. Unless otherwise noted, the MR spectra were recorded in CDCl 3. Chloroform (δ = 7.26 ppm) was used as internal standard in 1 H MR spectra, whereas CDCl 3 (δ = 77.2 ppm) was used as internal standard in 13 C MR spectra. 11 B chemical shifts are relative to Et 2 BF 3. Coupling constants (J) are given in Hertz (Hz). The terms m, s, d, t, q, quint. represent multiplet, singlet, doublet, triplet, quadruplet, quintuplet, respectively. The term br means that the signal is broad. In most of the cases, the carbenic carbon cannot be seen due to the coupling with the boron atom. HRMS were performed at the Institut de chimie moléculaire (FR 2769, UPMC). Pd(Ac) 2, RuPhos (2-dicyclohexylphosphino-2',6'-diisopropoxy-1,1'-biphenyl), Pd(dppf)Cl 2 and K 2 C 3 obtained from commercial sources were used as received. Microwave reactions were performed by using a Biotage Iniator Microwave Synthetizer
2 General procedure for the preparation of imidazolylidene borane complexes. Sublimed potassium tert-butoxide (316.8 mg, 2.82 mmol) was added at 0 C to a suspension of imidazolylium chloride salt 1 (2.35 mmol) in THF ( ml). After min, the reaction mixture was filtrated through a celite pad and rinsed with EtAc. Solvents were removed in vacuo, and the residue was suspended in dry hexane (19 ml). The borane (1M solution in THF) was added to the carbene suspension at 0 C and the resulting solution was allowed to warm to room temperature overnight. The solvents were evaporated to deliver the expected complexes after appropriate purification. Imidazolylidene borane complex-bph 3 (1): BPh 3 This carbene-borane was obtained as a white solid after recristallyzation (DCM/Et 2 /Pentane: 1/3/5). (95% yield). Mp C; IR (neat): ν = 56, 2965, 2929, 2871, 20, 1883, 18, 908 cm -1 ; 1 H MR (0 MHz, CDCl 3 ): δ 7. (t, J = 7.8 Hz, 2H, arom.), (m, H, arom.), (m, 8H, arom.), (m, 3H, arom.), 2.23 (sept., J = 6.9 Hz, 4H, CHMe 2 ), 1.25 (d, J = 6.9 Hz, 12H, CHMeMe), 1.09 (d, J = 6.9 Hz, 12H, CHMeMe) ; 13 C MR (0 MHz, CDCl 3 ): δ (C arom.), (CH arom.), (CH arom.), (CH arom.), (CH arom.), (CH arom.), (CH arom.), (CH arom.), 289 (CHMe 2 ), 24.7 (CHMeMe), 23.7 (CHMeMe) ; 11 B MR (BF 3 Et 2, 133 MHz, CDCl 3 ): δ (br s). 1 Arduengo, III, A. J.; Krafczyk, R.; Schmutzler, R. Tetrahedron 1999, 55,
3 Imidazolylidene borane complex-bet 3 (2): BEt 3 This carbene-borane was obtained analytically pure and used without further purification. (87% yield). Mp C; IR (neat): ν = 69, 2963, 2870, 1950, 18, 10, 1366 cm -1 ; 1 H MR (0 MHz, CDCl 3 ): δ 7. (t, J= 7.5 Hz, 2H, arom.), 7.19 (d, J = 7.5 Hz, 4H, arom.), 6. (s, 2H, =CH()), 3.06 (sept., J = 6.8 Hz, 4H, CHMe 2 ), 1.52 (d, J = 6.8 Hz, 12H, CHMeMe), 1.18 (t, J = 7.6 Hz, 9H, CH 2 Me), 1.07 (d, J = 7 Hz, 12H, CHMeMe), 0.56 (q, J = 7.6 Hz, 6H, CH 2 Me); 13 C MR (0 MHz, C 6 D 6 ): δ 146 (CiPr arom.), (C arom.), 1.4 (CH arom.), (=CH()), (CH arom.), 29 (CHMe 2 ), 26.4 (CHMeMe), 22.5 (CHMeMe), 14.9 (br CH 2 Me), 12.4 (CH 2 Me); 11 B MR (BF 3 Et 2, 133 MHz, CDCl 3 ): δ (br s). 3
4 Procedure A: Coupling from iodides and triflates. To Pd(dppf)Cl 2 (4 mg, 6 mol%), the substrate (0.082 mmol) and the HC-borane (0.082 mmol), THF (4 ml) and water (150 µl) were added. The reaction mixture was stirred at C for 1h or at 1 C under micro-wave for 15 min. The solvent was then evaporated in vacuo and the residue was purified by flash chromtography (Si 2, Pentane to Pentane/Et 2 : 99/1). Procedure B : Coupling from bromides and triflates. An Ace pressure tube (15 ml) was charged with Pd(Ac) 2 (5.6 mg, 5%), XPhos (23.8 mg, %), the substrate (0.5 mmol) and the HC-Borane (0.5 mmol). The pressure tube was sealed with a septum, evacuated under vacuum, and purged with argon (three times). Toluene (2.5 ml) and water (250 µl) were added and the pressure tube was sealed with a teflon cap. The reaction mixture was stirred at C for 24 h or at 1 C under micro-wave for min. The reaction mixture was cooled at room temperature, filtered through a small pad of silica (Pentane/Ether: 95/5) and the solvent was evaporated in vacuo. The residue was purified by flash chromatography (Si 2, Pentane to Pentane/Et 2 : 99/1). Procedure C : Coupling from chlorides. An Ace pressure tube (15 ml) was charged with Pd(Ac) 2 (11.2 mg, %), RuPhos (46.7 mg, %), the substrate (0.5 mmol) and the HC-Borane (0.5 mmol). The pressure tube was sealed with a septum, evacuated under vacuum, and purged with argon (three times). Toluene (2.5 ml) and water (250 µl) were added and the pressure tube was sealed with a teflon cap. The reaction mixture was stirred at C for 24 h or at 1 C under micro-wave for min. The reaction mixture was cooled at room temperature, filtered through a small pad of silica (Pentane/Ether: 95/5) and the solvent was evaporated in vacuo. The residue was purified by flash chromatography (Si 2, Pentane to Pentane/Et 2 : 99/1). 4
5 1,1 -Biphenyl-4-carboxylic acid, cyclohexyl ester (3): The product was obtained as a white solid. Mp C; IR (neat): ν = 2936, 2859, 17, 1112 cm -1 ; 1 H MR (0 MHz, CDCl 3 ): δ 8.12 (d, J= 8.1 Hz, 2H, arom.), (m, 4H, arom.), (m, 3H, arom.), (m, 1H, CH), (m, 2H, CH 2 ), (m, 2H, CH 2 ), (m, 3H, CH 2 ), (m, 3H, CH 2 ); 13 C MR (0 MHz, CDCl 3 ): δ (C=), (C arom.), 1.1 (C arom.), 1 (CH arom.), (CH arom.), 128 (CH arom.), (CH arom.), (CH arom.), 73 (CH), 31.6 (CH 2 ), 25.5 (CH 2 ), 23.6 (CH 2 ). 1-phenyl-2-(octyloxymethyl)benzene (4): The product was obtained as a colorless oil. IR (neat): ν =, 2924, 2853, 1951, 1895, 1812, 94 cm -1 ; 1 H MR (0 MHz, CDCl 3 ): δ (m, 1H, arom.), (m, 7H, arom.), (m, 1H, arom.), 4.39 (s, 2H, ArCH 2 ), 3.42 (t, J = 6.6 Hz, 2H, CH 2 CH 2 ), (m, 2H, CH 2 CH 2 ), (m, H, CH 2 ), 0.91 (t, J = 6.8 Hz, 3H, Me); 13 C MR (0 MHz, CDCl 3 ): δ (C arom.), 1.9 (C arom.), (C arom.), (CH arom.), (CH arom.), (CH arom.), (CH arom.), (CH arom.), (CH arom.), (CH arom.), 70.7 (ArCH 2 + CH 2 CH 2 ), 31.9 (CH 2 CH 2 ), 29.8 (CH 2 ), 29.5 (CH 2 ), 29.3 (CH 2 ), 26.3 (CH 2 ), 22.7 (CH 2 ), 14.1 (Me); HRMS calcd. For C 21 H 28 a ([M + a] + ): , found:
6 9-phenylphenanthrene (5): The product was obtained as a white solid. Mp 6-9 C; IR (neat): ν = 57, 1951, 1491, 1450 cm -1 ; 1 H MR (0 MHz, CDCl 3 ): δ 8.87 (d, J= 8 Hz, 1H, H4), 8.82 (d, J= 8 Hz, 1H, H11), 8.06 (d, J= 8 Hz, 1H, H14), 7.99 (d, J= 8 Hz, 1H, H1), (m, H, arom.); 13 C MR (0 MHz, CDCl 3 ): δ 1.8 (C15), (C9), (C6), (C7), 1.6 (C5), 1.0 (C19 + C17), (C8), (C18), (C + C16), (C1), (C14), (C2), (C13), (C3), (C12), (C), (C4), (C11) ; HRMS calcd. For C H + 14 ([M] + ): , found: cyclohexyl 4-ethylbenzoate (6): The product was obtained as a colorless oil. IR (neat): ν = 2932, 2858, 1711, 15 cm -1 ; 1 H MR (0 MHz, CDCl 3 ): δ 7.96 (d, J = 7.8 Hz, 2H, arom.), 7.25 (d, J = 7.8 Hz, 2H, arom.), (m, 1H, CH), 2.70 (q, J = 7.6 Hz, 2H, ArCH 2 ), (m, 2H, CH 2 ), (m, 2H, CH 2 ), (m, 3H, CH 2 ), (m, 3H, CH 2 ), 1.25 (t, J = 7.6 Hz, 3H, Me); 13 C MR (1 MHz, CDCl 3 ): δ (C=), (C arom.), (CH arom.), (C arom.), (CH arom.), 72.6 (CH), 31.5 (CH 2 + ArCH 2 ), 28.8 (CH 2 ), 25.4 (CH 2 ), 23.6 (CH 2 ), 15.2 (Me) ; HRMS calcd. For C 15 H 2 a ([M + a] + ): , found:
7 1-ethyl-2-(octyloxymethyl)benzene (7): The product was obtained as a colorless oil. IR (neat): ν = 21, 2957, 2925, 96 cm -1 ; 1 H MR (0 MHz, CDCl 3 ): δ 7.34 (d, J = 7.5 Hz, 1H, arom.), (m, 3H, arom.), 4.52 (s, 2H, ArCH 2 ), 3.48 (t, J = 6.6, 2H, CH 2 CH 2 ), 2.70 (q, J = 7.5 Hz, 2H, ArCH 2 Me), 1.62 (quint., J= 6.6 Hz, 2H, CH 2 CH 2 ), (m, 13H, CH 2 + ArCH 2 Me), 0.88 (t, J = 7.5 Hz, 3H, CH 2 CH 2 Me) ; 13 C MR (0 MHz, CDCl 3 ): δ (C arom.), (C arom.), (CH arom.), (CH arom.), (CH arom.), (CH arom.), 70.9 (CH 2 ), 70.6 (CH 2 ), 31.8 (CH 2 ), 29.8 (CH 2 ), 29.4 (CH 2 ), 29.3 (CH 2 ), 26.2 (CH 2 ), 25.2 (CH 2 ), 22.6 (CH 2 ), 15.1 (Me), 14.0 (Me) ; HRMS calcd. For C 17 H 28 a ([M + a] + ): , found: ethylphenanthrene (8): The product was obtained as a white solid. Mp C; IR (neat): ν = 76, 2965, 2933, 2874, 1948, 1917, 1900 cm -1 ; 1 H MR (0 MHz, CDCl 3 ): δ 8.74 (d, J= 9.2 Hz, 1H, H6), 8.67 (d, J = 7.6 Hz, 1H, H12), 8.13 (d, J = 9.2 Hz, 1H, H1), 7.84 (d, J= 7.6 Hz, 1H, H15), (m, 5H, arom.), 3.17 (q, J = 7.5 Hz, 2H, CH 2 ), 1.46 (t, J= 7.5 Hz, 3H, Me) ; 13 C MR (0 MHz, CDCl 3 ) : δ (C arom.), (C arom.), (C arom.), 1.6 (C arom.), (C arom.), (C15), (CH arom.), (CH arom.), (CH arom.), (CH arom.), (CH arom.), (CH arom.), (CH arom.), (CH arom.), 26 (CH 2 Me), 14.4 (CH 2 Me) ; HRMS calcd. For C 16 H 14 + ([M] + ): 6.90, found:
8 1,1-diphenylbut-1-ene (9): The product is obtained as a colorless oil. IR (neat): ν = 55, 22, 29, 2926, 2852, 1946, 1886, 16, 1731, 1443, 1663 cm -1 ; 1 H MR (0 MHz, CDCl 3 ): δ (m, H, arom.), 6.09 (t, J= 7.6 Hz, 1H, =CH), 2.15 (quint., J = 7.5 Hz, 2H, CH 2 Me), 1.07 (t, J = 7.5 Hz, 3H, Me); 13 C MR (0 MHz, CDCl 3 ): δ (C arom.), (C arom.), 1.2 (C arom.), (CH arom.), (CH arom.), (CH arom.), (CH arom.), (CH arom.), (CH arom.), (CH arom.), 23.2 (CH 2 Me), 14.5 (CH 2 Me). 8
9 9 BPh 3 1 H MR Integral BPh 3 13 C MR
10 11B en 8 scans, avec D1 = 2s 11 B MR BPh H routine : 8 scans Integral H MR BEt
11 JM277-13C C MR BEt B en 8 scans, avec D1 = 2s B MR BEt
12 Integral H MR C MR 3 3
13 Integral H routine : 8 scans 1 H MR C MR 4 4
14 1H routine : 8 scans H MR 5 Integral C routine : 32 scans C MR
15 Integral H MR C routine : 32 scans 13 C MR 6 6
16 1H routine : 8 scans Integral H MR C routine : 32 scans C MR
17 1H routine : 8 scans H MR C routine : 32 scans C MR
18 Integral JM193-pub 1 H MR JM193-pub 13 C MR 9 9
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