Inorganic Chemistry
Article
Tang, C. C.; Cinque, G.; Yang, S.; Schroder, M. Enhancement of CO2
Adsorption and Catalytic Properties by Fe-Doping of [Ga (OH) (L)]
(36) Ager, D. J.; Prakash, I.; Schaad, D. R. 1,2-Amino Alcohols and
Their Heterocyclic Derivatives as Chiral Auxiliaries in Asymmetric
Synthesis. Chem. Rev. 1996, 96, 835−876.
2
2
(
H L = Biphenyl-3,3′,5,5′-tetracarboxylic Acid), MFM-300(Ga ).
4
2
Inorg. Chem. 2016, 55, 1076−1088.
(37) Jacobsen, E. N. Asymmetric Catalysis of Epoxide Ring-Opening
Reactions. Acc. Chem. Res. 2000, 33, 421−431.
(
15) Dhakshinamoorthy, A.; Asiri, A. M.; Garcia, H. Mixed-metal or
(38) Chakraborti, A. K.; Rudrawar, S.; Kondaskar, A. An efficient
mixed-linker metal organic frameworks as heterogeneous catalysts.
synthesis of 2-amino alcohols by silica gel catalysed opening of epoxide
Catal. Sci. Technol. 2016, 6, 5238−5261.
rings by amines. Org. Biomol. Chem. 2004, 2, 1277−1280.
(
16) Ma, L.; Abney, C.; Lin, W. Enantioselective catalysis with
(39) Posner, G. H.; Rogers, D. Z. Organic reactions at alumina
homochiral metal-organic frameworks. Chem. Soc. Rev. 2009, 38,
248−1256.
17) Lee, J.; Farha, O. K.; Roberts, J.; Scheidt, K. A.; Nguyen, S. T.;
surfaces. Mild and selective opening of epoxides by alcohols, thiols,
benzeneselenol, amines, and acetic acid. J. Am. Chem. Soc. 1977, 99,
1
(
8
(
208−8214.
40) Chini, M.; Crotti, P.; Macchia, F. Metal salts as new catalysts for
mild and efficient aminolysis of oxiranes. Tetrahedron Lett. 1990, 31,
661−4664.
41) Sekar, S.; Singh, V. K. An Efficient Method for Cleavage of
Epoxides with Aromatic Amines. J. Org. Chem. 1999, 64, 287−289.
42) Auge, J.; Leroy, F. Lithium trifluoromethanesulfonate-catalysed
aminolysis of oxiranes. Tetrahedron Lett. 1996, 37, 7715−7716.
43) Curini, M.; Epifano, F.; Marcotullio, M. C.; Rosati, O.
Hupp, J. T. Metal−organic framework materials as catalysts. Chem. Soc.
Rev. 2009, 38, 1450−1459.
(
18) Feng, D.; Chung, W. C.; Wei, Z.; Gu, Z. Y.; Jiang, H. L.; Chen,
4
(
Y. P.; Darensbourg, D. J.; Zhou, H. C. Construction of Ultrastable
Porphyrin Zr Metal−Organic Frameworks through Linker Elimina-
tion. J. Am. Chem. Soc. 2013, 135, 17105−17110.
(
(
19) Zhang, M.; Bosch, M.; Gentle, T., III; Zhou, H. C. Rational
design of metal−organic frameworks with anticipated porosities and
functionalities. CrystEngComm 2014, 16, 4069−4083.
(
Zirconium Sulfophenyl Phosphonate as a Heterogeneous Catalyst in
the Preparation of β-Amino Alcohols from Epoxides. Eur. J. Org. Chem.
(
20) Tanabe, K. K.; Cohen, S. M. Modular, Active, and Robust Lewis
Acid Catalysts Supported on a Metal−Organic Framework. Inorg.
Chem. 2010, 49, 6766−6774.
2
(
001, 21, 4149−4152.
44) Chakraborti, A. K.; Kondaskar, A. ZrCl as a new and efficient
4
(
21) Garibay, S. J.; Wang, Z.; Cohen, S. M. Evaluation of
catalyst for the opening of epoxide rings by amines. Tetrahedron Lett.
003, 44, 8315−8319.
45) Iqbal, J.; Pandey, A. An unusual chemoselectivity in cobalt(II)
Heterogeneous Metal−Organic Framework Organocatalysts Prepared
by Postsynthetic Modification. Inorg. Chem. 2010, 49, 8086−8091.
2
(
(
22) Ma, L.; Wu, C. D.; Wanderley, M. M.; Lin, W. Single-Crystal to
chloride catalysed cleavage of oxiranes with anilines: A highly
regioselective synthesis of β-amino alcohols. Tetrahedron Lett. 1990,
31, 575−576.
Single-Crystal Cross-Linking of an Interpenetrating Chiral Metal−
Organic Framework and Implications in Asymmetric Catalysis. Angew.
Chem., Int. Ed. 2010, 49, 8244−8248.
́ ́
(46) Duran Pachon, L.; Gamez, P.; Van Brussel, J. J. M.; Reedijk, J.
(
23) Ma, L.; Falkowski, J. M.; Abney, C.; Lin, W. A series of
Zinc-catalyzed aminolysis of epoxides. Tetrahedron Lett. 2003, 44,
6025−6027.
isoreticular chiral metal−organic frameworks as a tunable platform for
asymmetric catalysis. Nat. Chem. 2010, 2, 838−846.
(47) Sabitha, G.; Kumar Reddy, G. S.; Bhaskar Reddy, K.; Yadav, J. S.
Vanadium(III) Chloride-Catalyzed Preparation of β-Amino Alcohols
from Epoxides. Synthesis 2003, 2298−2300.
(
24) Cohen, S. M. Postsynthetic Methods for the Functionalization
of Metal−Organic Frameworks. Chem. Rev. 2012, 112, 970−1000.
(
25) Wu, C.-D.; Lin, W. Heterogeneous Asymmetric Catalysis with
(48) Roy, S. R.; Nijamudheen, A.; Pariyar, A.; Ghosh, A.;
Vardhanapu, P. K.; Mandal, P. K.; Datta, A.; Mandal, S. K. Phenalenyl
in a Different Role: Catalytic Activation through the Nonbonding
Molecular Orbital. ACS Catal. 2014, 4, 4307−4319.
Homochiral Metal−Organic Frameworks: Network-Structure-De-
pendent Catalytic Activity. Angew. Chem., Int. Ed. 2007, 46, 1075−
1078.
(
49) Tanaka, K.; Oda, S.; Shiro, M. A novel chiral porous metal−
(
26) Kubelka, P.; Munk, F. Z. Ein beitrag zur optik der farbanstriche.
organic framework: asymmetric ring opening reaction of epoxide with
Technol. Phys. 1931, 12, 593−601.
amine in the chiral open space. Chem. Commun. 2008, 820−822.
(
(
27) SMART; Bruker AXS Inc.: Madison, WI, 2002.
28) SAINT; Bruker AXS Inc.: Madison, WI, 2008. SADABS; Bruker
(50) Ingleson, M. J.; Barrio, J. P.; Bacsa, J.; Dickinson, C.; Park, H.;
Rosseinsky, M. Generation of a solid Brønsted acid site in a chiral
AXS Inc.: Madison, WI, 2008.
29) Sheldrick, G. M. A short history of SHELX. Acta Crystallogr.,
Sect. A: Found. Crystallogr. 2008, 64, 112−122.
30) Kim, J.; Chen, B.; Reineke, T. M.; Li, H.; Eddaoudi, M.; Moler,
framework. Chem. Commun. 2008, 1287−1289.
(
(51) Jiang, D.; Mallat, T.; Krumeich, F.; Baiker, A. Copper-based
metal-organic framework for the facile ring-opening of epoxides. J.
Catal. 2008, 257, 390−395.
(
D. B.; O’Keeffe, D. B.; Yaghi, O. M. Assembly of Metal−Organic
Frameworks from Large Organic and Inorganic Secondary Building
Units: New Examples and Simplifying Principles for Complex
Structures. J. Am. Chem. Soc. 2001, 123, 8239−8247.
(
52) Dhakshinamoorthy, A.; Alvaro, M.; Garcia, H. Metal−Organic
Frameworks as Efficient Heterogeneous Catalysts for the Regiose-
lective Ring Opening of Epoxides. Chem. - Eur. J. 2010, 16, 8530−
8
536.
(
31) Gao, J.; Ye, K.; Yang, L.; Xiong, W.-W.; Ye, L.; Wang, Y.; Zhang,
(
53) Kumar, G.; Singh, A. P.; Gupta, R. Synthesis, Structures, and
Q. Growing Crystalline Zinc-1,3,5-benzenetricarboxylate Metal−
Organic Frameworks in Different Surfactants. Inorg. Chem. 2014, 53,
3+
3+
3+
Heterogeneous Catalytic Applications of {Co −Eu } and {Co −
Tb } Heterodimetallic Coordination Polymers. Eur. J. Inorg. Chem.
3+
6
(
91−693.
2
(
010, 2010, 5103−5112.
32) He, J.; Zhang, Y.; Pan, Q.; Yu, J.; Ding, H.; Xu, R. Three metal-
54) Biswas, S.; Maes, M.; Dhakshinamoorthy, A.; Feyand, M.; De
organic frameworks prepared from mixed solvents of DMF and HAc.
Vos, D. E.; Garcia, H.; Stock, N. Fuel purification, Lewis acid and
Microporous Mesoporous Mater. 2006, 90, 145−152.
aerobic oxidation catalysis performed by a microporous Co-BTT
(
33) Caskey, S. R.; Matzger, A. J. Selective Metal Substitution for the
3−
(
BTT = 1,3,5-benzenetristetrazolate) framework having coordina-
Preparation of Heterobimetallic Microporous Coordination Polymers.
tively unsaturated sites. J. Mater. Chem. 2012, 22, 10200−10209.
Inorg. Chem. 2008, 47, 7942−7944.
(55) Tanaka, K.; Otani, K.-I.; Murase, T.; Nishihote, S.; Urbanczyk-
(
34) Ma, R.; Liu, Z.; Takada, K.; Fukuda, K.; Ebina, Y.; Bando, Y.;
Lipkowska, Z. Enantioselective Ring-Opening Reaction of Epoxides
with MeOH Catalyzed by Homochiral Metal−Organic Framework.
Bull. Chem. Soc. Jpn. 2012, 85, 709−714.
(56) Dhakshinamoorthy, A.; Alvaro, M.; Garcia, H. Commercial
metal−organic frameworks as heterogeneous catalysts. Chem.
Commun. 2012, 48, 11275−11288.
Sasaki, T. Tetrahedral Co(II) Coordination in α-Type Cobalt
Hydroxide: Rietveld Refinement and X-ray Absorption Spectroscopy.
Inorg. Chem. 2006, 45, 3964−3969.
(
35) Taylor, J. M.; Thompson, R. C. Magnetic and Spectral Studies
on Cobalt(II) Fluorosulfate. Can. J. Chem. 1971, 49, 511−515.
G
Inorg. Chem. XXXX, XXX, XXX−XXX