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Volumn 10, Issue 7, 2008, Pages 1333-1336

Room-temperature Suzuki-Miyaura couplings in water facilitated by nonionic amphiphiles

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EID: 48949100374 PISSN: 15237060 EISSN: None Source Type: Journal
DOI: 10.1021/ol702714y Document Type: Article

Times cited : (177)

References (25)

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20
- 59849105207
- Using catalyst 6 under otherwise identical conditions, aryl bromides showed poor conversion to the corresponding biaryl products: 13 (27, 14 (39, 16 (21, and 21 43, as indicated by GC
- Using catalyst 6 under otherwise identical conditions, aryl bromides showed poor conversion to the corresponding biaryl products: 13 (27%), 14 (39%), 16 (21%), and 21 (43%), as indicated by GC.

21
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- To the best of our knowledge, the only publication describing the use of aryl perfluorooctylsulfonates in Suzuki-Miyaura cross-couplings: Zhang, W.; Chen, C. H.-T.; Lu, Y.; Nagashima, T. Org. Lett. 2004, 6, 1473-1476.
- To the best of our knowledge, the only publication describing the use of aryl perfluorooctylsulfonates in Suzuki-Miyaura cross-couplings: Zhang, W.; Chen, C. H.-T.; Lu, Y.; Nagashima, T. Org. Lett. 2004, 6, 1473-1476.

22
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- and references cited therein. Based on the reactivity differences observed between triflates and nonaflates; see
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23
- 59849126223
- n-C8F17SO2F is available for $165/mol (100 g, On that scale, CF3-SO2) 2O sells for $237/mol and n-C4F 9SO2F costs $256/mol. When purchasing 1 kg, the price drops to $127/mol and $145/mol, respectively, for the latter two. However, SciFinder gives no price quote for n-C8F 17SO2F on that scale
- 2F on that scale.

24
- 59849108397
- Sigma-Aldrich catalog #698717; available in May, 2008.
- Sigma-Aldrich catalog #698717; available in May, 2008.

25
- 1642320259
- Standard procedure for Suzuki-Miyaura in PTS/water. 4-Methoxy-2′-methylbiphenyl (23; Table 4, entry 4, To a 5 mL round-bottom flask was added a 15 mm long prolate spheroid magnetic stir bag. 5 (6 mg, 0.009 mmol, and 4-methoxyphenylboronic acid (114 mg, 0.75 mmol, Under a positive flow of argon while stirring were added each via syringe Et3N (0.21 mL, 1.5 mmol, aqueous PTS (1% w/w, 2 mL, and 2-chlorotoluene (60 μL, 0.51 mmol, The reaction was stirred at rt and conversion was monitored by GC. After 24 h the contents of the flask were diluted with brine and extracted three times with ethyl acetate. The solution obtained was dried over anhydrous MgSO4, filtered, and concentrated by rotary evaporation. The solid residue was purified by flash chromatography eluting with a gradient from 1/99 to 5/95 diethyl ether/petroleum ether to afford the product biaryl (86 mg, 85, as a white solid; 1H NMR (400 MHz, CDCl3) matches p
- 3) matches previously reported spectral data. (b) Tang, Z.-Y.; Hu, Q.-S. J. Am. Chem. Soc. 2004, 126, 3058-3059.

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