以邻溴苯甲醛为原料合成了一系列的羰基磷氧化物,用作铜催化的C-S偶联反应的新配体.在较温和的反应条件下可成功催化碘代芳烃或溴代芳烃与硫醇的偶联反应,收率最高达99%.
A series of carbonyl-phosphine oxide ligands were synthesized from 2-bromophenylaldehyde and used in Cu-catalyzed C-S coupling reactions.Aryl iodide and aryl bromide reacted with thiols efficiently upon catalysis under mild reaction conditions and a yield of up to 99% was obtained.
参考文献
[1] | Jones D N;Barton D H;Ollis D W.Comprehensive Organic Chemistry.Voi.3[M].New York:Pergamon Press,1979:33. |
[2] | Tiecco M.[J].SYNTHESIS-STUTTGART,1988:749. |
[3] | Rayner C M .[J].CONTEMPORARY ORGANIC SYNTHESIS,1996,3:499. |
[4] | Baird CP.;Rayner CM. .Synthesis of thiols, selenols, sulfides, selenides, sulfoxides, selenoxides, sulfones and selenones [Review][J].Journal of the Chemical Society, Perkin Transactions 1,1998(12):1973-2003. |
[5] | Procter D J .[J].Journal of the Chemical Society,Perkin Transactions,1999,1:641. |
[6] | Procter DJ. .The synthesis of thiols, selenols, sulfides, selenides, sulfoxides, selenoxides, sulfones and selenones [Review][J].Journal of the Chemical Society, Perkin Transactions 1,2000(6):835-871. |
[7] | Procter D J .[J].Journal of the Chemical Society,Perkin Transactions,2001,1:335. |
[8] | Herradura P S;Pendola K A;Guy R K .[J].Organic Letters,2000,2:2019. |
[9] | Migita T;Shimizu T;Asami Y;Shiobara J I Kato Y Kosugi M .[J].Bulletin of the Chemical Society of Japan,1980,53:1385. |
[10] | Fernández-Rodríguez M A;Shen Q L;Hartwig J F .[J].Chemistry-A European Journal,2006,12:7782. |
[11] | Fernández-Rodríguez M A;Shen Q L;Hartwig J F .[J].Journal of the American Chemical Society,2006,128:2180. |
[12] | Zhang Y;Ngeow K N;Ying J Y .[J].Organic Letters,2007,9:3495. |
[13] | Jammi S;Barua P;Rout L;Saha P Punniyamurthy T .[J].Tetrahedron Letters,2008,49:1484. |
[14] | Wong YC;Jayanth TT;Cheng CH .Cobalt-catalyzed aryl-sulfur bond formation[J].Organic letters,2006(24):5613-5616. |
[15] | Correa A;Carril M;Bolm C .[J].Angewandte Chemie International Edition,2008,47:2880. |
[16] | Palomo C;Oiarbide M;Lopez R;Gomez-Bengoa E .[J].Tetrahedron Letters,2000,41:1283. |
[17] | Kwong F Y;Buchwald S L .[J].Organic Letters,2002,4:3517. |
[18] | Enguehard-Gueiffier C;Thery I;Gueiffier A;Buchwald SL .A general and efficient method for the copper-catalyzed cross-coupling of amides and thiophenols with 6-halogenoimidazo[1,2-alpha]pyridines[J].Tetrahedron,2006(25):6042-6049. |
[19] | Gujadhur R K;Bates C G;Venkataraman D .[J].Organic Letters,2001,3:4315. |
[20] | Bates C G;Gujadhur R K;Venkataraman D .[J].Organic Letters,2002,4:2803. |
[21] | Deng W;Zou Y;Wang YF;Liu L;Guo QX .CuI-catalyzed coupling reactions of aryl iodides and bromides with thiols promoted by amino acid ligands[J].Synlett,2004(7):1254-1258. |
[22] | Chen YJ;Chen HH .1,1,1-tris(hydroxymethyl)ethane as a new, efficient, and versatile tripod ligand for copper-catalyzed cross-coupling reactions of aryl iodides with amides, thiols, and phenols[J].Organic letters,2006(24):5609-5612. |
[23] | Verma A K;Singh J;Chaudhary R .[J].Tetrahedron Letters,2007,48:7199. |
[24] | Rout L;Sen T K;Punniyamurthy T .[J].Angewandte Chemie International Edition,2007,46:5583. |
[25] | Ranu B C;Saha A;Jana R .[J].Advanced Synthesis and Catalysis,2007,349:2690. |
[26] | Carril M;SanMartin R;Dominguez E;Tellitu I .[J].Chemistry-A European Journal,2007,13:5100. |
[27] | Lv X;Bao WL .A beta-keto ester as a novel, efficient, and versatile ligand for copper(I)-catalyzed C-N, C-O, and C-S coupling reactions[J].The Journal of Organic Chemistry,2007(10):3863-3867. |
[28] | Prasad D J C;Naidu A B;Sekar G .[J].Tetrahedron Letters,2009,50:1411. |
[29] | Basu B;Mandal B;Das S;Kundu S .[J].Tetrahedron Letters,2009,50:5523. |
[30] | Feng, Y;Wang, HF;Sun, FF;Li, YM;Fu, XM;Jin, K .A highly efficient and widely functional-group-tolerant catalyst system for copper(I)-catalyzed S-arylation of thiols with aryl halides[J].Tetrahedron,2009(47):9737-9741. |
[31] | Zhu D;Xu L;Wu F;Wan BS .A mild and efficient copper-catalyzed coupling of aryl iodides and thiols using an oxime-phosphine oxide ligand[J].Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry,2006(32):5781-5784. |
[32] | Xu L;Zhu D;Wu F;Wang RL;Wan BS .Mild and efficient copper-catalyzed N-arylation of alkylamines and N-H heterocycles using an oxime-phosphine oxide ligand[J].Tetrahedron,2005(27):6553-6560. |
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