设计并合成了一种新型水溶性亚胺双齿配体Ⅰ,并得到其单晶结构.该配体具有半配位效应和绿色化学特征,与氯化钯组成的催化体系在空气和室温条件下,可有效催化乙醇水溶液中的溴代芳烃与芳基硼酸的Suzuki交叉偶联反应.在n(ArBr)=0.5mmol,n(ArB(OH)2)=0.75mmol,x(PdCl2)=1%,x(I)=2%,n(K2CO3)=1.0mmol,c(EtOH)=50%水溶液的优化条件下,经20min反应,分离收率即可达到99%.
参考文献
[1] | Miyaura N;Suzuki A .[J].Chemical Reviews,1995,95:2457. |
[2] | Miyaura N;Yamada K;Suzuki A .[J].Tetrahedron Letters,1979,20:3437. |
[3] | Billingsley K;Buchwald S L .[J].Journal of the American Chemical Society,2007,129:3358. |
[4] | Martin R;Buchwald S L .[J].Accounts of Chemical Research,2008,41:1461. |
[5] | Sawai K;Tatumi R;Nakahodo T;Fujihara H .[J].Angewandte Chemie International Edition,2008,47:6917. |
[6] | Molander G A;Canturk B .[J].Angew Chem Int End,2009,48:9240. |
[7] | Fujihara T;Yoshida S;Terao J;Tsuji Y .[J].Organic Letters,2009,11:2121. |
[8] | Ullah E;McNulty J;Robertson A .[J].Tetrahedron Letters,2009,50:5599. |
[9] | Uozumi Y;Matsuura Y;Arakawa T;Yamada Y M A .[J].Angewandte Chemie International Edition,2009,48:2708. |
[10] | Roy S;Plenio H .[J].Advanced Synthesis and Catalysis,2010,352:1014. |
[11] | Peh, G.-R.;Kantchev, E.A.B.;Er, J.-C.;Ying, J.Y. .Rational exploration of N-Heterocyclic carbene (NHC) palladacycle diversity: A highly active and versatile precatalyst for suzuki-miyaura coupling reactions of deactivated aryl and alkyl substrates[J].Chemistry: A European journal,2010(13):4010-4017. |
[12] | Lai YC;Chen HY;Hung WC;Lin CC;Hong FE .Palladium catalyzed Suzuki cross-coupling reactions using N,O-bidentate ligands[J].Tetrahedron,2005(40):9484-9489. |
[13] | Cui X;Li J;Zhang Z P;Fu Y Liu L Guo Q X .[J].Journal of Organic Chemistry,2007,72:9342. |
[14] | Poliakoff M;Fitzpatrick J M;Farren T R;Anastas P T .[J].Science,2002,297:807. |
[15] | DeSimone J M .[J].Science,2002,297:799. |
[16] | Alonso F;Beletskaya I P;Yus M .[J].Tetrahedron,2008,64:3047. |
[17] | Shi S Y;Zhang Y H .[J].Green Chemistry,2008,10:868. |
[18] | Yang H Q;Han X J;Ma Z C;Wang R Q Liu J Ji X F .[J].Green Chemistry,2010,12:441. |
[19] | Liu L F;Zhang Y H;Xin B W .[J].Journal of Organic Chemistry,2006,71:3994. |
[20] | Qiu HL;Sarkar SM;Lee DH;Jin MJ .Highly effective silica gel-supported N-heterocyclic carbene-Pd catalyst for Suzuki-Miyaura coupling reaction[J].Green chemistry,2008(1):37-40. |
[21] | Del Zotto A;Amoroso F;Baratta W;Rigo P .Very Fast Suzuki-Miyaura Reaction Catalyzed by Pd(OAc)(2) under Aerobic Conditions at Room Temperature in EGME/H2O[J].European journal of organic chemistry,2009(1):110-116. |
[22] | Bassetti M .Kinetic evaluation of ligand-hemilability in transition metal complexes[J].European journal of inorganic chemistry,2006(22):4473-4482. |
[23] | Weng ZQ;Teo SH;Hor TSA .Metal unsaturation and ligand hemilability in Suzuki coupling[J].Accounts of Chemical Research,2007(8):676-684. |
[24] | Pawar S S;Uppalla L S;Shingare M S;Thore S N .[J].Tetrahedron Letters,2008,49:5858. |
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