苯酚，烯醇，唑類，炔及其他C-, O-和N-負(fù)離子和三價(jià)或五價(jià)有機(jī)鉍試劑作用進(jìn)行芳基化的反應(yīng)。此類反應(yīng)在中性，酸性或堿性條件下都可以進(jìn)行。N芳基化可以在醋酸銅存在下，與Ar3Bi（可以由ArLi或ArMgX和三氯化鉍反應(yīng)制得）反應(yīng)實(shí)現(xiàn)，醇類的O芳基化可以在醋酸銅存在下和Ar4BiF反應(yīng)得到。[5][17]
反應(yīng)機(jī)理
反應(yīng)實(shí)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】
相關(guān)文獻(xiàn)
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
參考文獻(xiàn)
一、Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page 32-33.
二、Reactionflash APP
