毫无疑问,三位科学家发展的碳—碳原子的偶联方法极大地促进了现代有机合成化学的发展,它不仅表现在对合成科学上的巨大贡献,而且这项技术已在全球的科研、医药开发与生产、发光材料和电子工业材料等领域得到广泛应用。不过我们也还必须看到这些方法的局限性,一个挑战性的问题是这些反应中均要使用卤代烃、硼酸酯及其衍生物等作为反应原料的一部分,但是这些原料绝大多数并不是自然界存在的或者容易人工合成的物质,另外在得到期望产物的同时,也还伴随有卤代物等盐类副产物的生成。
参考文献:
[1] Segelstein B E;Butler T W;Chenard B L Equilibration of the osidative addition product of tetrakis(triphenylphosphine)palladium and electron-rich aryl halides to product scrambing in the stille reaction[外文期刊] 1995(01) doi:10.1021/jo00106a006
[2] 杜卫红;安忠维;徐茂梁 过渡金属催化不对称偶联反应及其在液晶合成中的应用1997(01)
[3] 陈新兵;安忠维;刘骞峰 超声条件下合成4-戊基(4′-丙基)双环己基联苯[期刊论文] -合成化学2000(04)
[4] H ECK R F. The palladium-catalyzed arylation of enol esters,ethers, and halid es. A new synthesis of 2-aryl aldehydes and ketones[ J ] . J Am Ch em Soc, 1968, 90: 5535-538.
[ 5 ] H ECK R F. Aromatic haloethylation with palladium and copper halides[ J] . J Am C hem Soc, 1968, 90: 5538-5542.
[ 6 ] HE CK R F. Th e add it ion of alkyl and arylpalladium chlorides to conjugated dienes [ J] . J Am C hem Soc, 1968, 90: 5542-5546.
[ 7 ] H ECK R F. A synthesis of diaryl ketones from arylm ercuricsalt s[ J ] . J Am Ch em Soc, 1968, 90: 5546-5548.
[ 8 ] MIZ OROKI T , MORI K, OZAKI A. Arylation of olef in with aryl iodid e catalyzed by palladium [ J ] . Bul l Chem Soc Jpn,1971, 44: 581-581.
[ 9 ] HE CK R F, NOLLEY J P. Palladium-catalyzed vinylic hydrogen substitution reactions with aryl , benzyl, and styryl halides[ J] . J Or g Ch em , 1972, 37: 2320 – 2322.
[10] KING A O, OKU KADO N, NEGISH I E I. Highly general stereo-, regio-, and chemo-selective synthesis of terminal and internal conjugated enynes by the Pd-catalysed reaction of alkynylzinc reagents with alkenyl halides [ J ] . J Ch em Soc,& 336Ch em Comm un, 1977: 683-684.
[11] NE GISHI E I. Palladium or nickel-catalyzed cross coupling.A new selective method f or carbon carbon bond formation[ J] . Acc Chem Res, 1982, 15: 340-348.