Organic Reactions catalyzed by rhenium carbonyl complexes
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1 Organic Reactions catalyzed by rhenium carbonyl complexes Fanyang Mo Dong group seminar Feb. 26, 2014 Ref: Kuninobu, Y.; Takai, K. Chem Rev. 2011, 111,
2 Accidentally found by Ogawa in 1908, and officially discovered by Noddack, Tacke, and Berg in
3 General Applications in Industry Filament Jet engine (high melting point 3186 o C) Petroleum purification (Platinum-rhenium catalysts) 3
4 Contents 1. Introduction 2. C C bond formation 2.1 Friedel-Crafts 2.2 Nucleophilic addition 2.3 Annulations 2.4 C H bond activation 2.5 C C bond cleavage 3. Conclusion 4
![1. Introduction [Xe] 4f¹⁴ 5d⁵ 6s² Commercially available Rhenium carbonyl complexes.](/docs-images/83/88223101/images/5-0.jpg "Four notable features o Hard Lewis acidity (O, N, halides) o Soft Lewis acidity (unsaturated compounds) o Ability to activate")
5 1. Introduction [Xe] 4f¹⁴ 5d⁵ 6s² Commercially available Rhenium carbonyl complexes. Four notable features o Hard Lewis acidity (O, N, halides) o Soft Lewis acidity (unsaturated compounds) o Ability to activate C H bond o Promote oxidative cyclization 5
6 2. C C bond formation 2.1 Friedel-Crafts 2.2 Nucleophilic addition 2.3 Annulations 2.4 C H bond activation 2.5 C C bond cleavage 6
7 2.1 Friedel-Crafts Reactions Kusama, H.; Narasaka, K. Bull. Chem. Soc. Jpn. 1995, 68, Nishiyama, Y.; Kakushou, F.; Sonoda, N. Bull. Chem. Soc. Jpn. 2000, 73,
8 2.1 Friedel-Crafts Reactions Hua, R.; He, J.; Sun, H. Chin. J. Chem. 2007, 25, 132. o Regio-selectivity Kuninobu, Y.; Matsuki, T.; Takai, K. J. Am. Chem. Soc. 2009, 131,
9 2. C C bond formation 2.1 Friedel-Crafts 2.2 Nucleophilic addition 2.3 Annulations 2.4 C H bond activation 2.5 C C bond cleavage 9
10 2.2 Nucleophilic addition to carbonyl compounds Knoevenagle condensation o o No solvent No base Zuo, W.-X.; Hua, R.; Qiu, X. Synth. Commun. 2004, 34, Nishiyama, Y.; Kakushou, F.; Sonoda, N. Tetrahedron Lett. 2005, 46,
11 2.2 Nucleophilic addition to carbonyl compounds Mukaiyama Aldol reaction Nishiyama, Y.; Kaiba, K.; Umeda, R. Tetrahedron Lett. 2010, 51, 793. o Mechanism: Kuninobu, Y.; Ishii, E.; Takai, K. Angew. Chem., Int. Ed. 2007, 46,
12 2.2 Nucleophilic addition to carbonyl compounds o Imine as electrophile o Mechanism: For H-alkynyl-rhenium complexes, see: a) K.-W. Lee; W. T. Pennington; A. W. Cordes; T. L. Brown, J. Am. Chem. Soc. 1985, 107, 631. b) K.-W. Lee; T. L. Brown, Organometallics 1985, 4, Kuninobu, Y.; Inoue, Y.; Takai, K. Chem. Lett. 2006, 35,
13 2.2 Nucleophilic addition to carbonyl compounds o Enantioselective addition Bolm, C.; Kesselgruber, M.; Hermanns, N.; Hildebrand, J. P.; Raabe, G. Angew. Chem., Int. Ed. 2001, 40,
14 2.2 Nucleophilic addition to C C unsaturated bond Kuninobu, Y.; Kawata, A.; Takai, K. Org. Lett. 2005, 7,
15 2.2 Nucleophilic addition to C C unsaturated bond Kuninobu, Y.; Yamashita, A.; Yamamoto, S.-i.; Yudha, S. S.; Takai, K. Synlett 2009,
16 2. C C bond formation 2.1 Friedel-Crafts 2.2 Nucleophilic addition 2.3 Annulations 2.4 C H bond activation 2.5 C C bond cleavage 16
17 2.3 Annulations Quiz1: The mechanisms for both 2a and 3a formation? Kusama, H.; Yamabe, H.; Onizawa, Y.; Hoshino, T.; Iwasawa, N. Angew. Chem., Int. Ed. 2005, 44,
18 2.3 Annulations o Mechanism: Saito, K.; Onizawa, Y.; Kusama, H.; Iwasawa, N. Chem.-Eur. J. 2010, 16,
19 2.3 Annulations o [3+2] Kusama, H.; Miyashita, Y.; Takaya, J.; Iwasawa, N. Org. Lett. 2006, 8,
20 2.3 Annulations OL 2005 Slide 14 o Mechanism: Kuninobu, Y.; Nishi, M.; Yudha, S. S.; Takai, K. Org. Lett. 2008, 10, Tsuji, H.; Yamagata, K.-i.; Fujimoto, T.; Nakamura, E. J. Am. Chem. Soc. 2008, 130,
21 2.3 Annulations Previous slide Quiz 2: Product 54% Kuninobu, Y.; Iwanaga, T.; Nishi, M.; Takai, K. Chem. Lett. 2010, 39,
22 2. C C bond bond formation 2.1 Friedel-Crafts 2.2 Nucleophilic addition 2.3 Annulations 2.4 C H bond activation 2.5 C C bond cleavage Re(0,I), Ru(0), Rh(I) Rh(III), Pd(II) 22
23 2.4 C H bond activation o Sp3 C H borylation Chen, H.; Hartwig, J. F. Angew. Chem., Int. Ed. 1999, 38,
24 2.4 C H bond activation Kuninobu, Y.; Kawata, A.; Takai, K. J. Am. Chem. Soc. 2005, 127, Kuninobu, Y.; Nishina, Y.; Shouho, M.; Takai, K. Angew. Chem., Int. Ed. 2006, 45,
25 2.4 C H bond activation VII VIII VIII more metalicity 5 6 Less electronegativity Re Ru, Rh 25
26 2.4 C H bond activation o Addition to polar unsaturated bonds Isocyanates Aldehydes Kuninobu, Y.; Tokunaga, Y.; Kawata, A.; Takai, K. J. Am. Chem. Soc. 2006, 128, 202. Quiz 3 Kuninobu, Y.; Nishina, Y.; Nakagawa, C.; Takai, K. J. Am. Chem. Soc. 2006, 128,
27 2.4 C H bond activation Kuninobu, Y.; Fujii, Y.; Matsuki, T.; Nishina, Y.; Takai, K. Org. Lett. 2009, 11,
28 2.4 C H bond activation o Discovery o Mechanism Kuninobu, Y.; Nishina, Y.; Matsuki, T.; Takai, K. J. Am. Chem. Soc. 2008, 130,
29 2. C C bond formation 2.1 Friedel-Crafts 2.2 Nucleophilic addition 2.3 Annulations 2.4 C H bond activation 2.5 C C bond cleavage 29
30 2.4 C C bond cleavage o Substrate scope o Mechanism Retroaldol Kuninobu, Y.; Kawata, A.; Takai, K. J. Am. Chem. Soc. 2006, 128,
31 2.4 C C bond cleavage OL 2005 JACS 2006 Vitali, D.; Calderazzo, F. Gazz. Chim. Ital. 1972, 102, 587. Kuninobu, Y.; Kawata, A.; Nishi, M.; Yudha, S. S.; Chen, J.-j.; Takai, K. Chem. Asian J. 2009, 4,
32 2.4 C C bond cleavage Kuninobu, Y.; Kawata, A.; Nishi, M.; Takata, H.; Takai, K.Chem. Commun. 2008,
33 Contents 1. Introduction 2. C C bond formation 2.1 Friedel-Crafts 2.2 Nucleophilic addition 2.3 Annulations 2.4 C H bond activation 2.5 C C bond cleavage 3. Conclusion 33
34 4. Conclusion Prior to 2000 Used as hard Lewis acid catalysts o o o Friedel-Crafts reactions Aldol reactions Knoevenagel reactions Not interfered by a small amount of water Since about 2000 Have also been employed as soft Lewis acids o Nucleophilic additions to alkynes or allenes o Cycloisomerization of enynes o Cyclization reactions Many similar reactions were previously known to be promoted by other transition metals Since 2005 C-H and C-C bond cleavage o o C-H oxidative addtion Unique reactivity
35 35
36 36
37 Answers for quiz 1 Kusama, H.; Yamabe, H.; Onizawa, Y.; Hoshino, T.; Iwasawa, N. Angew. Chem., Int. Ed. 2005, 44,
38 Answers for quiz 2 Kuninobu, Y.; Iwanaga, T.; Nishi, M.; Takai, K. Chem. Lett. 2010, 39,
39 Answers for quiz 3 Kuninobu, Y.; Nishina, Y.; Nakagawa, C.; Takai, K. J. Am. Chem. Soc. 2006, 128,
40 2.2 Nucleophilic addition to carbonyl compounds Fukumoto, Y.; Daijo, M.; Chatani, N. J. Am. Chem. Soc. 2012, 134,
41 2.3 Annulations o Mechanism: Chatani, N.; Kataoka, K.; Murai, S. J. Am. Chem. Soc. 1998, 120,
42 3. C hetero bond formation Zhao, W.-G.; Hua, R. Eur. J. Org. Chem. 2006, Ouh, L. L.; Müller, T. E.; Yan, Y. K. J. Organomet. Chem. 2005, 690, Yudha, S. S.; Kuninobu, Y.; Takai, K. Org. Lett. 2007, 9,
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