A General Thermolabile Protecting Group Strategy for Organocatalytic Metal-Organic Frameworks

被引：302

作者：

Lun, David J. ^{[1
]}

Waterhouse, Geoffrey I. N. ^{[2
]}

Telfer, Shane G. ^{[1
]}

机构：

[1] Massey Univ, Inst Fundamental Sci, MacDiarmid Inst Adv Mat & Nanotechnol, Palmerston North, New Zealand

[2] Univ Auckland, Dept Chem, Auckland, New Zealand

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 15期

关键词：

HETEROGENEOUS ASYMMETRIC CATALYSIS; PROLINE-DERIVATIVES; ALDOL REACTIONS; DESIGN; AMINE; SIZE; MOFS;

D O I：

10.1021/ja202223d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We present a general strategy for incorporating organocatalytic moieties into metal organic frameworks (MOFs). The organocatalytic units are protected by a thermolabile protecting group during MOF synthesis and then unveiled by a simple postsynthetic heating step. The strategy is exemplified using a thermolabile tert-butoxycarbonyl (Boc) protecting group for a proline moiety, the removal of which endows the resulting cubic zinc(II) IRMOF with catalytic activity for asymmetric aldol reactions. The bulky Boc groups also prevent framework interpenetration, producing open MOFs that can admit relatively large substrates.

引用

页码：5806 / 5809

页数：4

共 40 条

[1] Postsynthetic Modification Switches an Achiral Framework to Catalytically Active Homochiral Metal-Organic Porous Materials [J].

Banerjee, Mainak ;

Das, Sunirban ;

Yoon, Minyoung ;

Choi, Hee Jung ;

Hyun, Myung Ho ;

Park, Se Min ;

Seo, Gon ;

Kim, Kimoon .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (22) :7524-+

[2] Post-Synthetic Modification of Tagged Metal-Organic Frameworks [J].

Burrows, Andrew D. ;

Frost, Christopher G. ;

Mahon, Mary F. ;

Richardson, Christopher .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (44) :8482-8486

[3] Sulfur-tagged metal-organic frameworks and their post-synthetic oxidation [J].

Burrows, Andrew D. ;

Frost, Christopher G. ;

Mahon, Mary F. ;

Richardson, Christopher .

CHEMICAL COMMUNICATIONS, 2009, (28) :4218-4220

[4] A metal-organic framework material that functions as an enantioselective catalyst for olefin epoxidation [J].

Cho, So-Hye ;

Ma, Baoqing ;

Nguyen, SonBinh T. ;

Hupp, Joseph T. ;

Albrecht-Schmitt, Thomas E. .

CHEMICAL COMMUNICATIONS, 2006, (24) :2563-2565

[5] Organocatalysis with proline derivatives: improved catalysts for the asymmetric Mannich, nitro-Michael and aldol reactions [J].

Cobb, AJA ;

Shaw, DM ;

Longbottom, DA ;

Gold, JB ;

Ley, SV .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (01) :84-96

[6] Engineering Metal Organic Frameworks for Heterogeneous Catalysis [J].

Corma, A. ;

Garcia, H. ;

Llabres i Xamena, F. X. L. I. .

CHEMICAL REVIEWS, 2010, 110 (08) :4606-4655

[7] Cu and Au Metal-Organic Frameworks Bridge the Gap between Homogeneous and Heterogeneous Catalysts for Alkene Cyclopropanation Reactions [J].

Corma, Avelino ;

Iglesias, Marta ;

Llabres i Xamena, Francese X. ;

Sanchez, Felix .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (32) :9789-9795

[8] Homochiral Metal-Organic Frameworks for Heterogeneous Asymmetric Catalysis [J].

Dang, Dongbin ;

Wu, Pengyan ;

He, Cheng ;

Xie, Zhong ;

Duan, Chunying .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (41) :14321-14323

[9] Thermo labile Groups in Metal-Organic Frameworks: Suppression of Network Interpenetration, Post-Synthetic Cavity Expansion, and Protection of Reactive Functional Groups [J].

Deshpande, Rajesh K. ;

Minnaar, Jozeph L. ;

Telfer, Shane G. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (27) :4598-4602

[10] Systematic design of pore size and functionality in isoreticular MOFs and their application in methane storage [J].

Eddaoudi, M ;

Kim, J ;

Rosi, N ;

Vodak, D ;

Wachter, J ;

O'Keeffe, M ;

Yaghi, OM .

SCIENCE, 2002, 295 (5554) :469-472

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