Barton芳基化反应

苯酚，烯醇，唑类，炔及其他C-, O-和N-负离子和三价或五价有机铋试剂作用进行芳基化的反应。此类反应在中性，酸性或碱性条件下都可以进行。N芳基化可以在醋酸铜存在下，与Ar3Bi（可以由ArLi或ArMgX和三氯化铋反应制得）反应实现，醇类的O芳基化可以在醋酸铜存在下和Ar4BiF反应得到。[5][17]

反应机理

反应实例

1-Phenyl-2-naphthol (2). To a stirred solution of Ph3BiCl2 (550 mg, 1.07 mmol) and 2-naphthol 1 (144 mg, 1 mmol) in THF (1 M) at 20 ℃ under Ar was added tetramethyl-2-t-butylguanidine (TMBG, 500 mg, 0.11 mmol). After 5 h stirring, usual workup and chromatography (silica gel, Et2O:hexane 1:4) 198 mg of 2 (90%) was isolated.

【Barton DHR, Tet Lett., 1986, 27, 3615,3619】

【Journal of Organometallic Chemistry, 2006, 691, 2386-2393】

相关文献

1 Barton DHR J Chem Soc Chem Comm 1983 939

2 Barton DHR J Chem Soc Perkin Trans 1985 2657,2667

3 Barton DHR Tet Lett 1986 27 3615,3619

4 Barton DHR Tet lett 1987 28 887

5 Barton DHR Tetrahedron 1988 44 3039

6R Finet J-P Chem Rev 1989 89 1487

7* Moloney MG Tet Asymm 1996 7 2551

8 Barton DHR Tetrahedron 1997 53 4137

9 Finet J-P Tetrahedron 1998 54 4313

10 Finet J-P Tet Lett 1999 40 2747

11R Konopelski JP Tetrahedron 2001 57 5683

12 Jonathan CM Org Lett 2002 4 631

13 Boyer G Synth Comm 2002 32 2893

14 Finet J-P Eur J Org Chem 2004 2040

15 Mukaiyama T ARKIVOC 2007 vii 254

16 Moloney MG Tet Lett 2009 50 4523

17 Nicolaou KC Angew Chem Int 2009 48 6870

参考文献

一、Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page 32-33.

二、Reactionflash APP