中文
Announcement
More
Progress in Chemistry 2006, Vol. 18 Issue (06): 752-760 Previous Articles   Next Articles

• Review •

Transition-Metal Catalyzed α-Arylation of Carbonyl Derivatives and Compounds with Acidic Hydrogen

Junfang Gong;Chen Xu;Yangjie Wu**   

  1. Department of Chemistry, Zhengzhou University, Zhengzhou 450052, China
  • Received: Revised: Online: Published:
  • Contact: Yangjie Wu
PDF ( 2093 ) Cited
Export

EndNote

Ris

BibTeX

Advances in the transition-metal catalyzed α-arylation of carbonyl derivatives and compounds with acidic hydrogen are reviewed. By using sterically hindered, electron-rich alkylphosphines and N-heterocyclic carbenes(NHC), this process has encompassed a broad range of substrates including ketones, aldehydes, esters, amides, malonates, nitrocompounds, nitriles and sulfones.

CLC Number: 

[ 1 ] Shen T Y. Angew. Chem. Int . Ed. Engl . , 1972 , 11 : 460 —472
[ 2 ] Harrington P J , Lodewijk E. Org. Process. Res. Dev. , 1997 , 1 :72 —76
[ 3 ] Yamada T , Omote Y, Yamanaka Y, Miyazawa T , Kuwata S.Synthesis , 1998 , 991 —998
[ 4 ] Abramovitch R A , Barton D H R , Finet J P. Tetrahedron , 1988 ,44 : 3039 —3071
[ 5 ] Norris R K, Trost B M, Semmelhack M F. Comprehensive Organic Synthesis. New York : Pergamon Press , 1991. Vol . 4 , Chapter 212
[ 6 ] March J . Advanced Organic Chemistry , 4th ed. New York :Wiley , 1992. 1281 —1289
[ 7 ] Negishi E I , Akiyoshi K. Chem. Lett . , 1987 , 1007 —1009
[ 8 ] Heck R K. J . Am. Chem. Soc. , 1968 , 90 : 5535 —5538
[ 9 ] Bellina F , Carpita A , Rossi R. Synthesis , 2004 , 15 : 2419 —2440
[10] Littke A F , Fu G C. Angew. Chem. Int . Ed. Engl . , 2002 , 41 :4176 —4211
[11] Miura M, Nomura M. Top. Curr. Chem. , 2002 , 219 : 211 —241
[12] Hamann B C , Hartwig J F. J . Am. Chem. Soc. , 1997 , 119 :12382 —12383
[13] Palucki M, Buchwald S L. J . Am. Chem. Soc. , 1997 , 119 :11108 —11109
[14] Satoh T , Kawamura Y, Miura M, Nomura M. Angew. Chem.Int . Ed. Engl . , 1997 , 36 : 1740 —1742
[15] Culkin D A , Hartwig J F. Acc. Chem. Res. , 2003 , 36 : 234 —245
[16] 邵志会( Shao Z H) , 张洪彬( Zhang H B) . 有机化学(Chineses Journal of Organic Chemistry) , 2005 , 25 (3) : 282 —289
[17] Burkhardt E R , Bergman R G, Heathcock C H. Organometallics ,1990 , 9 : 30 —44
[18] Ruiz J , Martínez M T , Rodríguez V , et al . J . Chem. Soc. ,Dalton. Trans. , 2004 , 3521 —3527
[19] Hamashima Y, Sodeoka M. Chem. Rec. , 2004 , 4 : 231 —242
[20] Bordwell F G. Acc. Chem. Res. , 1988 , 21 : 456 —463
[21] Whiteside G M, Gaasch J F , Stedronsky E R. J . Am. Chem.Soc. , 1972 , 94 : 5258 —5270
[22] Louie J , Hartwig J F. J . Am. Chem. Soc. , 1995 , 117 :11598 —11599
[23] Kawatsura M, Hartwig J F. J . Am. Chem. Soc. , 1999 , 121 :1473 —1478
[24] Fox J M, Huang X H , Chieffi A , Buchwald S L. J . Am. Chem.Soc. , 2000 , 122 : 1360 —1370
[25] Kataoka N , Shelby Q , Stambuli J P , Hartwig J F. J . Org.Chem. , 2002 , 67 : 5553 —5566
[26] Ehrentraut A , Zapf A , Beller M. Adv. Synth. Catal . , 2002 ,344 : 209 —217
[27] Viciu M S , Germaneau R F , Nolan S P. Org. Lett . , 2002 , 4 :4053 —4056
[28] Viciu M S , Gemaneau R F , Navarro-Fernandez O , et al .Organometallics , 2002 , 21 : 5470 —5472
[29] Viciu M S , Kelly R A , Stevens E D , et al . Org. Lett . , 2003 ,5 : 1479 —1482
[30] Adjabeng G, Brenstrum T , Frampton C S , et al . J . Org. Chem. ,2004 , 69 : 5082 —5086
[31] Rutherford J L , Rainka M P , Buchwald S L. J . Am. Chem.Soc. , 2002 , 124 : 15168 —15169
[32] Wang D K, Wu Z. Chem. Commun. , 1999 , 529 —530
[33] Churruca F , Sanmartin R , Tellitu I , Dominguez E. Org. Lett . ,2002 , 4 : 1591 —1594
[34] Clough J M, Worthington P A , Gravestock M B. EP 0 114 487 ,1984
[35] Culshaw A J , Gull P , Hallett A , et al . WO 076 946 , 2002
[36] Prashad M, Liu Y G, Repic O. Adv. Synth. Catal . , 2003 , 345 :533 —536
[37] Terao Y, Satoh T , Miura M, Nonura M. Bull . Chem. Soc.Jpn. , 1999 , 72 : 2345 —2350
[38] SoléD , Vallverdú L , Solans X, Bardia M F , Bonjoch J . J . Am.Chem. Soc. , 2003 , 125 : 1587 —1594
[39] SoléD , Diaba F , Bonjoch J . J . Org. Chem. , 2003 , 68 : 5746 —5749
[40] ! hman J , Wolfe J P , Troutman M V , Buchwald S L. J . Am.Chem. Soc. , 1998 , 120 : 1918 —1919
[41] Hamada T , Chieffer A , ! hman J , Buchwald SL. J . Am. Chem.Soc. , 2002 , 124 : 1261 —1268
[42] Malinakova H C. Chem. Eur. J . , 2004 , 10 : 2636 —2646
[43] Muratake H , Nakai H. Tetrahedron Lett . , 1999 , 40 : 2355 —2358
[44] Terao Y, Fukuoka Y, Satoh T , Miura M, Nomura M. Tetrahedron Lett . , 2002 , 43 : 101 —104
[45] Terao Y, Satoh T , Miura M, Nomura M. Tetrahedron Lett . ,1998 , 39 : 6203 —6206
[46] Nejjar A , Pinel C J , Djakovitch L. Adv. Synth. Catal . , 2003 ,345 : 612 —619
[47] Koech P K, Krische M J . J . Am. Chem. Soc. , 2004 , 126 :5350 —5351
[48] Lee S , Beare N A , Hartwig J F. J . Am. Chem. Soc. , 2001 ,123 : 8410 —8411
[49] Moradi W A , Buchwald S L. J . Am. Chem. Soc. , 2001 , 123 :7996 —8002
[50] Goossen L J . Chem. Commun. , 2001 , 669 —670
[51] Lloyd-Jones G C. Angew. Chem. Int . Ed. Engl . , 2002 , 41 :953 —956
[52] Jorgensen M, Sunwoo L , Liu X X, et al . J . Am. Chem. Soc. ,2002 , 124 : 12557 —12565
[53] Zeevaart J G, Parkinson C J , Koning C B. Tetrahedron Lett . ,2004 , 45 : 4261 —4264
[54] Liu X X, Deng M Z. Chem. Commun. , 2002 , 622 —623
[55] Hama T J , Liu X X, Culkin D A , Hartwig J F. J . Am. Chem.Soc. , 2003 , 125 : 11176 —11177
[56] Liu X X, Hartwig J F. J . Am. Chem. Soc. , 2004 , 126 : 5182 —5191
[57] Bentz E , Moloney M G, Westaway S M. Tetrahedron. Lett . ,2004 , 45 : 7395 —7397
[58] Spielvogel D J , Buchwald S L. J . Am. Chem. Soc. , 2002 , 124 :3500 —3501
[59] Liu X X, Hartwig J F. Org. Lett . , 2003 , 5 : 1915 —1918
[60] Shaughnessy K H , Hamann B C , Hartwig J F. J . Org. Chem. ,1998 , 63 : 6546 —6553
[61] Lu T Y, Xue C H , Luo F T. Tetrahedron Lett . , 2003 , 44 :1587 —1590
[62] Cossy J , Filippis A D , Pardo D G. Org. Lett . , 2003 , 5 : 3037 —3039
[63] Filippis A D , Pardo D G, Cossy J . Tetrahedron , 2004 , 60 :9757 —9767
[64] Lee S , Hartwig J F. J . Org. Chem. , 2001 , 66 : 3402 —3415
[65] O’Donnell M, Bennett WD , Bruder WA , et al . J . Am. Chem.Soc. , 1988 , 110 : 8520 —8525
[66] Gaertzen O , Buchwald S L. J . Org. Chem. , 2002 , 67 : 465 —475
[67] Kawaguchi S. Coord. Chem. Rev. , 1986 , 70 : 51 —84
[68] Djakovitch L , Kêhler K. J . Organomet . Chem. , 2000 , 606 :101 —107
[69] Beare N A , Hartwig J F. J . Org. Chem. , 2002 , 67 : 541 —555
[70] Stambuli J P , Stauffer S R , Shaughnessy K H , Hartwig J F. J .Am. Chem. Soc. , 2001 , 123 : 2677 —2678
[71] Özdemir I , Yigit M, μetinkaya E , Cetinkaya B. Tetrahedron Lett . , 2004 , 45 : 5823 —5825
[72] Hennessy E , Buchwald S L. Org. Lett . , 2002 , 4 : 269 —272
[73] Okuro K, Furuune M, Miure M, Nomura M. J . Org. Chem. ,1993 , 58 : 7606 —7607
[74] Sotaoh T , Inoh J , Kawamura Y, Miure M, Nomura M. Bull .Chem. Soc. Jpn. , 1998 , 71 : 2239 —2246
[75] Stauffer S R , Beare N A , Stambull J P , Hartwig J F. J . Am.Chem. Soc. , 2001 , 123 : 4641 —4642
[76] Culkin D A , Hartwig J F. J . Am. Chem. Soc. , 2002 , 124 :9330 —9331
[77] You J S , Verkade J G. J . Org. Chem. , 2003 , 68 : 8003 —8007
[78] You J S , Verkade J G. Angew. Chem. Int . Ed. Engl . , 2003 ,42 : 5051 —5053
[79] Gao C W, Tao X C , Liu T P , Huang J L , Qian YL. Chin. J .Chem. , 2002 , 20 : 819 —821
[80] Gao C W, Tao X C , Qian Y L , Huang J L. Chem. Commun. ,2003 , 1444 —1445
[81] Inoh J I , Satoh T , Pivsa A S , Miura M, Nomura M. Tetrahedron Lett . , 1998 , 39 : 4673 —4676
[82] Vogl E M, Buchwald S L. J . Org. Chem. , 2002 , 67 : 106 —111
[83] Kashin A N , Mitin A V , Beletskaya I P , Wife R. Tetrahedron Lett . , 2002 , 14 : 2539 —2542
[84] Mitin A V , Kashin A N , Beletskaya I P. J . Organomet . Chem. ,2004 , 689 : 1085 —1090
[85] Zeevaart J G, Parkinson C J , Koning C B. Tetrahedron Lett . ,2005 , 46 : 1597 —1599
[86] Cho G Y, Bolm C. Org. Lett . , 2005 , 7 : 1351 —1354

[1] Lei Pengfei, Zhang Wensheng, Kuang Chunxiang, Jiang Yubo. Synthesis of Terminal Arylacetylenes [J]. Progress in Chemistry, 2016, 28(2/3): 317-327.
[2] . Progress in Palladium??Catalyzed Amination of Aryl Halides [J]. Progress in Chemistry, 2005, 17(02): 286-292.
[3] Li Yanyun,Xia Chungu**,Xie Baohan. Synthesis of Chiral Phosphine Ligands and Their Applications in Asymmetric Catalysis [J]. Progress in Chemistry, 2000, 12(03): 305-.