Communication

You have free access to this content

Symbiotic Catalysis Relay: Molecular Oxygen Activation Catalyzed by Multiple Small Molecules at Ambient Temperature and its Mechanism

Cangbai Qiu¹,
Liqun Jin²,
Zhiliang Huang²,
Zhenquan Tang¹,
Prof. Aiwen Lei^2,3,*,
Zhenlu Shen¹,
Nan Sun¹,
Weimin Mo¹,
Baoxiang Hu¹,
Prof. Xinquan Hu^1,3,*

Article first published online: 14 NOV 2011

DOI: 10.1002/cctc.201100300

Issue

ChemCatChem

Volume 4, Issue 1, pages 76–80, January 2, 2012

Additional Information

How to Cite

Qiu, C., Jin, L., Huang, Z., Tang, Z., Lei, A., Shen, Z., Sun, N., Mo, W., Hu, B. and Hu, X. (2012), Symbiotic Catalysis Relay: Molecular Oxygen Activation Catalyzed by Multiple Small Molecules at Ambient Temperature and its Mechanism. ChemCatChem, 4: 76–80. doi: 10.1002/cctc.201100300

Author Information

¹
College of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou 310014 (P.R. China), Fax: (+86) 571-88320103
²
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072 (P.R. China)
³
State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000 (P.R. China)

Email: Prof. Aiwen Lei (aiwenlei@whu.edu.cn), Prof. Xinquan Hu (xinquan@zjut.edu.cn)

^*College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072 (P.R. China)

Publication History

Issue published online: 27 DEC 2011
Article first published online: 14 NOV 2011
Manuscript Revised: 10 OCT 2011
Manuscript Received: 26 AUG 2011

Funded by

National Natural Science Foundations of China. Grant Numbers: 20772111, 20876149, 21025206, 20832003, 20972118, 20772093
MOST of China. Grant Number: 2011CB808600
the Fundamental Research Funds for the Central Universities
Program for New Century Excellent Talents in University
Ministry of Education of China

ARTICLE TOOLS

View Full Article with Supporting Information (HTML) Get PDF (657K)

1
1a
A. L. Feig, S. J. Lippard, Chem. Rev. 1994, 94, 759–805;
1b
S. Ferguson-Miller, G. T. Babcock, Chem. Rev. 1996, 96, 2889–2908;
1c
M. E. Andersson, M. Högbom, A. Rinaldo-Matthis, K. K. Andersson, B.-M. Sjöberg, P. Nordlund, J. Am. Chem. Soc. 1999, 121, 2346–2352;
1d
Q. Su, J. P. Klinman, Biochemistry 1999, 38, 8572–8581;
1e
M. Costas, M. P. Mehn, M. P. Jensen, L. Que, Chem. Rev. 2004, 104, 939–986;
1f
D. A. Nicewicz, D. W. C. MacMillan, Science 2008, 322, 77–80;
1g
K. P. Jensen, C. B. Bell, M. D. Clay, E. I. Solomon, J. Am. Chem. Soc. 2009, 131, 12155–12171;
1h
A. Poater, L. Cavallo, Inorg. Chem. 2009, 48, 4062–4066;
1i
R. L. Shook, A. S. Borovik, Inorg. Chem. 2010, 49, 3646–3660;
1j
W. J. Song, M. S. McCormick, R. K. Behan, M. H. Sazinsky, W. Jiang, J. Lin, C. Krebs, S. J. Lippard, J. Am. Chem. Soc. 2010, 132, 13582–13585.
2
S. S. Stahl, Science 2005, 309, 1824–1826.
3
3a
L. I. Simándi in Advances in Catalytic Activation of Dioxygen by Metal Complexes (Ed.: L. I. Simándi), Kluwer Academic Publishers, Boston, 2003;
3b
E. V. Rybak-Akimova in Physical Inorganic Chemistry: Reactions, Processes, and Applications (Ed.: A. Bakac), Wiley, Hoboken, 2010, pp. 109–188;
- CrossRef
3c
M. Lanfranchi, L. Prati, M. Rossi, A. Tiripicchio, J. Chem. Soc. Chem. Commun. 1993, 1698–1699;
3d
G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Science 2000, 287, 1636–1639;
- CrossRef,
- PubMed,
- CAS,
- ADS
3e
B. M. Choudary, M. L. Kantam, A. Rahman, C. V. Reddy, K. K. Rao, Angew. Chem. 2001, 113, 785–788;
Direct Link:
Angew. Chem. Int. Ed. 2001, 40, 763–766;
Direct Link:
3f
D. R. Jensen, J. S. Pugsley, M. S. Sigman, J. Am. Chem. Soc. 2001, 123, 7475–7476;
3g
B. A. Steinhoff, I. A. Guzei, S. S. Stahl, J. Am. Chem. Soc. 2004, 126, 11268–11278;
3h
M. J. Schultz, R. S. Adler, W. Zierkiewicz, T. Privalov, M. S. Sigman, J. Am. Chem. Soc. 2005, 127, 8499–8507;
3i
E. A. Katayev, K. Severin, R. Scopelliti, Y. A. Ustynyuk, Inorg. Chem. 2007, 46, 5465–5467;
3j
R. L. Shook, S. M. Peterson, J. Greaves, C. Moore, A. L. Rheingold, A. S. Borovik, J. Am. Chem. Soc. 2011, 133, 5810–5817.
4
4a
P. I. Dalko, L. Moisan, Angew. Chem. 2004, 116, 5248–5286;
Direct Link:
Angew. Chem. Int. Ed. 2004, 43, 5138–5175;
Direct Link:
4b
Y. Huang, A. M. Walji, C. H. Larsen, D. W. C. MacMillan, J. Am. Chem. Soc. 2005, 127, 15051–15053;
4c
T. D. Beeson, A. Mastracchio, J.-B. Hong, K. Ashton, D. W. C. MacMillan, Science 2007, 316, 582–585;
4d
B. List, Chem. Rev. 2007, 107, 5413–5415;
4e
C. F. Barbas, III, Angew. Chem. 2008, 120, 44–50;
Direct Link:
Angew. Chem. Int. Ed. 2008, 47, 42–47;
Direct Link:
4f
L. Lu, Y. Cao, X. Liu, J. An, C. Yao, Z. Ming, W. Xiao, J. Am. Chem. Soc. 2008, 130, 6946–6948;
4g
L. S. Hegedus, J. Am. Chem. Soc. 2009, 131, 17995–17997;
4h
Z. Shao, H. Zhang, Chem. Soc. Rev. 2009, 38, 2745–2755;
4i
C. Grondal, M. Jeanty, D. Enders, Nat. Chem. 2010, 2, 167–178;
4j
W. Liu, H. Cao, H. Zhang, H. Zhang, K. H. Chung, C. He, H. Wang, F. Y. Kwong, A. Lei, J. Am. Chem. Soc. 2010, 132, 16737–16740.
5
5a
J. Muldoon, S. N. Brown, Org. Lett. 2002, 4, 1043–1045;
5b
N. Jiang, A. J. Ragauskas, ChemSusChem 2008, 1, 823–825;
Direct Link:
5c
M. Shibuya, Y. Osada, Y. Sasano, M. Tomizawa, Y. Iwabuchi, J. Am. Chem. Soc. 2011, 133, 6497–6500.
6
T. B. Cai, P. G. Wang, A. A. Holder in Nitric Oxide Donors: For Pharmaceutical and Biological Applications (Eds.: P. G. Wang, T. B. Cai, N. Taniguchi), Wiley-VCH, Weinheim, 2005. pp. 3–32.
7
7a
T. Fey, H. Fischer, S. Bachmann, K. Albert, C. Bolm, J. Org. Chem. 2001, 66, 8154–8159;
7b
M. Fernández, G. Tojo in Oxidation of Alcohols to Aldehydes and Ketones: A Guide to Current Common Practice (Ed.: G. Tojo, M. Fernández), Springer, New York, 2006. pp. 241–254.
8
8a
J. Piera, J.-E. Bäckvall, Angew. Chem. 2008, 120, 3558–3576;
Direct Link:
Angew. Chem. Int. Ed. 2008, 47, 3506–3523;
Direct Link:
8b
J. Piera, K. Närhi, J.-E. Bäckvall, Angew. Chem. 2006, 118, 7068–7071;
Direct Link:
Angew. Chem. Int. Ed. 2006, 45, 6914–6917;
Direct Link:
8c
G. Csjernyik, A. H. Ĕll, L. Fadini, B. Pugin, J.-E. Bäckvall, J. Org. Chem. 2002, 67, 1657–1662;
8d
K. Bergstad, S. Y. Jonsson, J.-E. Bäckvall, J. Am. Chem. Soc. 1999, 121, 10424–10425;
8e
J.-E. Baeckvall, R. B. Hopkins, H. Grennberg, M. M. Mader, A. K. Awasthi, J. Am. Chem. Soc. 1990, 112, 5160–5166;
- CrossRef,
- CAS
8f
J.-E. Baeckvall, A. K. Awasthi, Z. D. Renko, J. Am. Chem. Soc. 1987, 109, 4750–4752.
- CrossRef,
- CAS
9
9a
R. Liu, X. Liang, C. Dong, X. Hu, J. Am. Chem. Soc. 2004, 126, 4112–4113;
9b
R. Liu, C. Dong, X. Liang, X. Wang, X. Hu, J. Org. Chem. 2005, 70, 729–731.
10
Y. Xie, W. Mo, D. Xu, Z. Shen, N. Sun, B. Hu, X. Hu, J. Org. Chem. 2007, 72, 4288–4291.
11
X. He, Z. Shen, W. Mo, N. Sun, B. Hu, X. Hu, Adv. Synth. Catal. 2009, 351, 89–92.
Direct Link:
12
12a
G. Yang, W. Wang, W. Zhu, C. An, X. Gao, M. Song, Synlett 2010, 437–440;
12b
C. Miao, L. He, J. Wang, F. Wu, J. Org. Chem. 2010, 75, 257–260;
12c
B. Karimi, E. Farhangi, Chem. Eur. J. 2011, 17, 6056–6060;
Direct Link:
12d
T. Yakura, A. Ozono, Adv. Synth. Catal. 2011, 353, 855–859;
Direct Link:
12e
S. Wertz, A. Studer, Adv. Synth. Catal. 2011, 353, 69–72;
Direct Link:
12f
C. Miao, L. He, J. Wang, J. Wang, Adv. Synth. Catal. 2009, 351, 2209–2216;
Direct Link:
12g
Y. Kuang, H. Rokubuichi, Y. Nabae, T. Hayakawa, M.-a. Kakimoto, Adv. Synth. Catal. 2010, 352, 2635–2642;
Direct Link:
12h
Y. Jing, J. Jiang, B. Yan, S. Lu, J. Jiao, H. Xue, G. Yang, G. Zheng, Adv. Synth. Catal. 2011, 353, 1146–1152;
Direct Link:
12i
L. Di, Z. Hua, Adv. Synth. Catal. 2011, 353, 1253–1259;
Direct Link:
12j
W. Yin, C. Chu, Q. Lu, J. Tao, X. Liang, R. Liu, Adv. Synth. Catal. 2010, 352, 113–118.
Direct Link:
13
For a detailed experimental procedure, see the Supporting Information.
14
Based on the aerobic oxidation experiments and kinetic studies, pressurized oxygen is not an essential condition; however, for a neat aerobic oxidation reaction, pressurized oxygen would be beneficial to improve the reaction conversion using 100 mmol of alcohol substrate.
15
H. Miyamura, M. Shiramizu, R. Matsubara, S. Kobayashi, Angew. Chem. 2008, 120, 8213–8215;
Direct Link:
Angew. Chem. Int. Ed. 2008, 47, 8093–8095.
Direct Link:

View Full Article with Supporting Information (HTML) Get PDF (657K)

JOURNAL TOOLS

JOURNAL MENU

FIND ISSUES

FIND ARTICLES

GET ACCESS

FOR CONTRIBUTORS

ABOUT THIS JOURNAL

SPECIAL FEATURES

Symbiotic Catalysis Relay: Molecular Oxygen Activation Catalyzed by Multiple Small Molecules at Ambient Temperature and its Mechanism

ChemCatChem

How to Cite

Author Information

Publication History

Funded by

ARTICLE TOOLS

More content like this

JOURNAL TOOLS

JOURNAL MENU

FIND ISSUES

FIND ARTICLES

GET ACCESS

FOR CONTRIBUTORS

ABOUT THIS JOURNAL

SPECIAL FEATURES

Symbiotic Catalysis Relay: Molecular Oxygen Activation Catalyzed by Multiple Small Molecules at Ambient Temperature and its Mechanism

ChemCatChem

How to Cite

Author Information

Publication History

Funded by

SEARCH

SEARCH BY CITATION

ARTICLE TOOLS

More content like this