以3-溴苯甲醚为原料合成了新型双膦配体6,6'-二甲氧基-2,2'-二(二-N-咔唑基膦)-1,1'联苯,并将该配体与钯组成的配合物用于对溴苯甲醚和苯硼酸的suzuki偶联反应,考察了溶剂、碱、底物/催化剂摩尔比、膦/钯摩尔比对偶联反应的影响.结果表明,该催化体系在1,4-二氧六环中催化对溴苯甲醚和苯硼酸的Suzuki偶联反应得到99%的分离产率.同时,该催化体系用于其它芳基溴和苯硼酸的Suzuki偶联反应也表现出很好的催化性能,即使芳基溴有较大的空间位阻或具有取代基也能获得很好的结果.
参考文献
| [1] | Miyaura N;Suzuki A .[J].Chemical Reviews,1995,95:2457. |
| [2] | Suzuki A .[J].Journal of Organometallic Chemistry,1999,576:147. |
| [3] | Hassan J;Sevignon M;Gozzi C;Schulz E Lemaire M .[J].Chemical Reviews,2002,102:1359. |
| [4] | Chemler SR;Trauner D;Danishefsky SJ .The B-alkyl Suzuki-Miyaura cross-coupling reaction: Development, mechanistic study, and applications in natural product synthesis [Review][J].Angewandte Chemie International Edition,2001(24):4544-4568. |
| [5] | Kotha S;Lahiri K;Kashinath D .[J].Tetrahedron,2002,58:9633. |
| [6] | Surry D S;Buchwald S L .[J].Angewandte Chemie International Edition,2008,47:6338. |
| [7] | Martin R;Buchwald S L .[J].Accounts of Chemical Research,2008,41:1461. |
| [8] | Clarke M L;Cole-Hamilton D J;Woolins J D.[J].Journal of the Chemical Society,Dalton Transactions,2001:2721. |
| [9] | Schareina T;Kempe R .[J].Angewandte Chemie International Edition,2002,41:1521. |
| [10] | Urgaonkar S;Nagarajan M;Verkade J G .[J].Tetrahedron Letters,2002,43:8921. |
| [11] | Clarke M L;Cole-Hamilton D J;Slawin A M Z;Woolins J D.[J].Chemical Communications,2000:2065. |
| [12] | Chang J;Wang F;Xu J H;Pan Y Zhang Z G .[J].Tetrahedron Letters,2003,44:7095. |
| [13] | Cho SD;Kim HK;Yim HS;Kim MR;Lee JK;Kim JJ;Yoon YJ .Suzuki-Miyaura coupling reaction of aryl chlorides using di(2,6-dimethylmorpholino)phenylphosphine as ligand[J].Tetrahedron,2007(6):1345-1352. |
| [14] | Farina V;Krishnamurihy V;Scott W J.The Stille Reaction in Organic Reactions[M].New York:John Wiley and Sons,Inc,1997 |
| [15] | Ma M L;Peng Z H;Chen L;Guo Y Chen H Li X J .[J].Chinese Journal of Chemistry,2006,24:1391. |
| [16] | Koh JH.;Larsen AO.;White PS.;Gagne MR. .Disparate roles of chiral ligands and molecularly imprinted cavities in asymmetric catalysis and chiral poisoning[J].Organometallics,2002(1):7-9. |
| [17] | Miyaura N;de Meijere A;Diederich F.Metal-Catalyzed Cross-Coupling Reactions[M].Weinheim:Willy-VCH,2004:41. |
| [18] | Bei X H;Turner HW;Weinberg W H;Guram A S Petersen J L .[J].Journal of Organic Chemistry,1999,64:6797. |
| [19] | Kataoka N.;Shelby Q.;Stambuli JP.;Hartwig JF. .Air stable, sterically hindered ferrocenyl dialkylphosphines for palladium-catalyzed C-C, C-N, and C-O bond-forming cross-couplings[J].The Journal of Organic Chemistry,2002(16):5553-5566. |
| [20] | Dai Q;Gao W Z;Liu D;Kapes L M Zhang X M .[J].Journal of Organic Chemistry,2006,71:3928. |
| [21] | Ohta H;Tokunaga M;Obora Y;Iwai T;Iwasawa T;Fujihara T;Tsuji Y .A bowl-shaped phosphine as a ligand in palladium-catalyzed Suzuki-Miyaura coupling of aryl chlorides: Effect of the depth of the bowl[J].Organic letters,2007(26):89-92. |
| [22] | Fujihara T;Yoshida S;Terao J;Tsuji Y .[J].Organic Letters,2009,11:2121. |
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