Selective Catalytic Monoreduction of Phthalimides and Imidazolidine‐2,4‐diones

邻苯二甲酰亚胺 咪唑啉 催化作用 组合化学 化学 有机化学 邻苯二甲酰亚胺
作者
Shoubhik Das,Daniele Addis,Leif R. Knöpke,Ursula Bentrup,Kathrin Junge,Angelika Brückner,Matthias Beller
出处
期刊:Angewandte Chemie [Wiley]
卷期号:50 (39): 9180-9184 被引量:123
标识
DOI:10.1002/anie.201104226
摘要

Angewandte Chemie International EditionVolume 50, Issue 39 p. 9180-9184 Communication Selective Catalytic Monoreduction of Phthalimides and Imidazolidine-2,4-diones† Shoubhik Das, Shoubhik Das Leibniz-Institut für Katalyse e.V. (LIKAT) an der Universität Rostock, Albert-Einstein-Straße 29a, 18059 Rostock (Germany) http://www.catalysis.deSearch for more papers by this authorDr. Daniele Addis, Dr. Daniele Addis Leibniz-Institut für Katalyse e.V. (LIKAT) an der Universität Rostock, Albert-Einstein-Straße 29a, 18059 Rostock (Germany) http://www.catalysis.deSearch for more papers by this authorLeif R. Knöpke, Leif R. Knöpke Leibniz-Institut für Katalyse e.V. (LIKAT) an der Universität Rostock, Albert-Einstein-Straße 29a, 18059 Rostock (Germany) http://www.catalysis.deSearch for more papers by this authorDr. Ursula Bentrup, Dr. Ursula Bentrup Leibniz-Institut für Katalyse e.V. (LIKAT) an der Universität Rostock, Albert-Einstein-Straße 29a, 18059 Rostock (Germany) http://www.catalysis.deSearch for more papers by this authorDr. Kathrin Junge, Dr. Kathrin Junge Leibniz-Institut für Katalyse e.V. (LIKAT) an der Universität Rostock, Albert-Einstein-Straße 29a, 18059 Rostock (Germany) http://www.catalysis.deSearch for more papers by this authorProf. Dr. Angelika Brückner, Prof. Dr. Angelika Brückner Leibniz-Institut für Katalyse e.V. (LIKAT) an der Universität Rostock, Albert-Einstein-Straße 29a, 18059 Rostock (Germany) http://www.catalysis.deSearch for more papers by this authorProf. Dr. Matthias Beller, Corresponding Author Prof. Dr. Matthias Beller [email protected] Leibniz-Institut für Katalyse e.V. (LIKAT) an der Universität Rostock, Albert-Einstein-Straße 29a, 18059 Rostock (Germany) http://www.catalysis.deLeibniz-Institut für Katalyse e.V. (LIKAT) an der Universität Rostock, Albert-Einstein-Straße 29a, 18059 Rostock (Germany) http://www.catalysis.deSearch for more papers by this author Shoubhik Das, Shoubhik Das Leibniz-Institut für Katalyse e.V. (LIKAT) an der Universität Rostock, Albert-Einstein-Straße 29a, 18059 Rostock (Germany) http://www.catalysis.deSearch for more papers by this authorDr. Daniele Addis, Dr. Daniele Addis Leibniz-Institut für Katalyse e.V. (LIKAT) an der Universität Rostock, Albert-Einstein-Straße 29a, 18059 Rostock (Germany) http://www.catalysis.deSearch for more papers by this authorLeif R. Knöpke, Leif R. Knöpke Leibniz-Institut für Katalyse e.V. (LIKAT) an der Universität Rostock, Albert-Einstein-Straße 29a, 18059 Rostock (Germany) http://www.catalysis.deSearch for more papers by this authorDr. Ursula Bentrup, Dr. Ursula Bentrup Leibniz-Institut für Katalyse e.V. (LIKAT) an der Universität Rostock, Albert-Einstein-Straße 29a, 18059 Rostock (Germany) http://www.catalysis.deSearch for more papers by this authorDr. Kathrin Junge, Dr. Kathrin Junge Leibniz-Institut für Katalyse e.V. (LIKAT) an der Universität Rostock, Albert-Einstein-Straße 29a, 18059 Rostock (Germany) http://www.catalysis.deSearch for more papers by this authorProf. Dr. Angelika Brückner, Prof. Dr. Angelika Brückner Leibniz-Institut für Katalyse e.V. (LIKAT) an der Universität Rostock, Albert-Einstein-Straße 29a, 18059 Rostock (Germany) http://www.catalysis.deSearch for more papers by this authorProf. Dr. Matthias Beller, Corresponding Author Prof. Dr. Matthias Beller [email protected] Leibniz-Institut für Katalyse e.V. (LIKAT) an der Universität Rostock, Albert-Einstein-Straße 29a, 18059 Rostock (Germany) http://www.catalysis.deLeibniz-Institut für Katalyse e.V. (LIKAT) an der Universität Rostock, Albert-Einstein-Straße 29a, 18059 Rostock (Germany) http://www.catalysis.deSearch for more papers by this author First published: 24 August 2011 https://doi.org/10.1002/anie.201104226Citations: 110 † This work was funded by the State of Mecklenburg-Western Pomerania, the BMBF, and the DFG (Leibniz Prize). We thank Dr. W. Baumann, Dr. C. Fischer, S. Buchholz, S. Schareina, A. Kammer, A. Koch, B. Wendt, S. Rossmeisl, and K. Mevius (all at the LIKAT) for their excellent technical and analytical support. Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract Fluoride's new role: Selective and efficient monoreductions of imides can be achieved with polymethylhydrosiloxane (PMHS) and tetra-n-butylammonium fluoride (TBAF) as catalyst (see scheme). The system is characterized by good chemoselectivity, operational simplicity, and functional-group tolerance; a concise mechanistic proposal was possible from in situ spectroscopic investigations. Supporting Information Detailed facts of importance to specialist readers are published as "Supporting Information". Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Filename Description anie_201104226_sm_miscellaneous_information.pdf3.9 MB miscellaneous_information Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. References 1 1aJ. T. Link, S. Raghavan, S. J. Danishefsky, J. Am. Chem. Soc. 1995, 117, 552; 1bU. C. Yoon, Y. X. Jin, S. W. Oh, C. H. Park, J. H. Park, C. F. Campana, X. Cai, E. N. Duesler, P. S. Mariano, J. Am. Chem. Soc. 2003, 125, 10664; 1cD. L. Comins, S. Schilling, Y. Zhang, Org. Lett. 2005, 7, 95; 1dH. Wehlan, E. Jezek, N. Lebrasseur, G. Pave, E. Roulland, A. J. P. White, J. N. Burrows, A. G. M. Barett, J. Org. Chem. 2006, 71, 8151; 1eJ. K. Kim, Y. H. Kim, H. T. Nam. B. T. Kim, J. N. Heo, Org. Lett. 2008, 10, 3543. 2aT. Honma, K. Hayashi, T. Aoyama, N. Hashimoto, T. Machida, K. Fukasawa, T. Z. Iwama, C. Ikeura, M. Ikuta, I. Suzuki-Takahashi, Y. Iwasawa, T. Hayama, S. Nishimura, H. Morishima, J. Med. Chem. 2001, 44, 4615; 2bJ. Guillamuel, S. Léonce, A. Pierré, P. Renard, B. Pfeiffer, P. B. Arimondo, C. Monneret, Eur. J. Med. Chem. 2006, 41, 379; 2cS. Lee, C. Shinji, K. Ogura, M. Shimizu, S. Maeda, M. Sato, M. Yoshida, Y. Hashimotoa, H. Miyachi, Bioorg. Med. Chem. Lett. 2007, 17, 4895; 2dD. Hamprecht, F. Micheli, G. Tedesco, A. Checchia, D. Donati, M. Petrone, S. Terrenia, M. Wood, Bioorg. Med. Chem. Lett. 2007, 17, 428; 2eT. Lubbers, P. Angehrn, H. Gmunderb, S. Herzig, Bioorg. Med. Chem. Lett. 2007, 17, 4708; 2fN. Kanamitsu, T. Osaki, Y. Itsuji, M. Yoshimura, H. Tsujimoto, M. Soga, Chem. Pharm. Bull. 2007, 55, 1682; 2gJ. H. Lee, S. R. Byeon, Y. S. Kim, S. J. Lim, S. J. Oh, K. H. Dae, H. C. Moon, B. Y. Chung, D. J. Kim, Bioorg. Med. Chem. Lett. 2008, 18, 5701. 3 3aV. G. Stygles, J. F. Newton, J. B. Hook, Res. Commun. Chem. Pathol. Pharmacol. 1977, 18, 329; 3bR. Ceserani, M. Colombo, V. Mandelli, Prostaglandins Med. 1979, 2, 337; 3cY. Nozawa, M. Ito, K. Sugawara, K. Hanada, K. Mizoue, J. Antibiot. 1997, 50, 641; 3dD. M. Vigushin, R. C. Coombes, Anticancer Drugs. 2002, 13, 1; 3eN. J. Lawrence, J. Liddle, S. Bushell, D. A. Jackson, J. Org. Chem. 2002, 67, 457; 3fS. Inoue, R. Kim, Y. Hoshino, K. Honda, Chem. Commun. 2006, 1974; 3gS. Fustero, J. Moscardo, D. Jiménez, M. D. Pérez- Carrion, M. Sánchez-Roselló, C. Pozo, Chem. Eur. J. 2008, 14, 9868; 3hJ. C. Chen, A. K. Oyelere, Bioorg. Med. Chem. Lett. 2009, 19, 6588; 3iS. Ito, Y. Hirata, Y. Nagatomi, A. Satoh, G. Suzuki, T. Kimura, A. Satow, S. Maehara, H. Hikichi, M. Hata, H. Ohta, H. Kawamoto, Bioorg. Med. Chem. Lett. 2009, 19, 5310. 4aY. Kuminobu, Y. Tokunaga, A. Kawata, K. Taka, J. Am. Chem. Soc. 2006, 128, 202; 4bK. Orito, M. Miyazawa, T. Nakamura, A. Horibata, H. Ushito, H. Nagashaki, M. Yuguchi, S. Yamashita, T. Yamazaki, M. Tokuda, J. Org. Chem. 2006, 71, 5951; 4cK. Kobyashi, M. Hase, K. Hashimoto, S. Fujita, M. Tanmatsu, O. Morikawa, H. Konishi, Synthesis 2006, 15, 2493; 4dD. A. Klump, Y. Zhang, M. J. O'Conor, P. M. Esteves, L. S. Almeid, Org. Lett. 2007, 9, 3085; 4eX. Huang, J. Xu, J. Org. Chem. 2009, 74, 8859. 5M. H. Norman, D. J. Minick, G. C. Rigdon, J. Med. Chem. 1996, 39, 149. 6 6aP. S. Anderson, M. E. Christy, C. D. Colton, W. Halczenco, G. S. Ponticelli, K. L. Shepard, J. Org. Chem. 1979, 44, 1519; 6bS. Feng, C. A. Panetta, D. E. Graves, J. Org. Chem. 2001, 66, 612. 7 7aF. Marshall, J. Am. Chem. Soc. 1956, 78, 3696; 7bK. C. Schreiber, V. P. Fernandez, J. Org. Chem. 1961, 26, 1744; 7cH. Okamura, H. Shimizu, Y. Nakamura, T. Iwagawa, M. Nakatani, Tetrahedron Lett. 2000, 41, 4147; 7dT. Inagaki, Y. Yamada, L. T. Phong, A. Furuta, J.-i. Ito, H. Nishiyama, Synlett 2009, 253. 8D. E. Patton, R. S. Drago, J. Chem. Soc. Perkin Trans. 1 1993, 1611. 9R. Aoun, J. L. Renaud, P. H. Dixneuf, C. Bruneau, Angew. Chem. 2005, 117, 2057; Angew. Chem. Int. Ed. 2005, 44, 2021. 10aM. Ito, A. Sakaguchi, C. Kobayashi, T. Ikariya, J. Am. Chem. Soc. 2007, 129, 290; 10bS. Takebayashi, J. M. John, S. H. Bergens, J. Am. Chem. Soc. 2010, 132, 12832. 11 11aS. Enthaler, D. Addis, K. Junge, G. Erre, M. Beller, Chem. Eur. J. 2008, 14, 9491; 11bS. Enthaler, K. Junge, D. Addis, G. Erre, M. Beller, ChemSusChem 2008, 1, 1006; 11cD. Addis, S. Enthaler, K. Junge, B. Wendt, M. Beller, Tetrahedron Lett. 2009, 50, 3654. 12 12aD. J. Parks, W. E. Piers, J. Am. Chem. Soc. 1996, 118, 9440; 12bS. Hanada, E. Tsutsumi, Y. Motoyama, H. Nagashima, J. Am. Chem. Soc. 2009, 131, 15032; 12cY. Sunada, H. Kawakami, T. Imaoka, Y. Motoyama, H. Nagashima, Angew. Chem. 2009, 121, 9675; Angew. Chem. Int. Ed. 2009, 48, 9511; 12dD. V. Gutsulyak, G. I. Nikonov, Angew. Chem. 2010, 122, 7715; Angew. Chem. Int. Ed. 2010, 49, 7553; 12eD. V. Gutsulyak, A. Est, G. I. Nikonov, Angew. Chem. 2011, 123, 1420; Angew. Chem. Int. Ed. 2011, 50, 1384. 13 13aS. Zhou, K. Junge, D. Addis, S. Das, M. Beller, Angew. Chem. 2009, 121, 9671; Angew. Chem. Int. Ed. 2009, 48, 9507; 13bS. Das, D. Addis, S. Zhou, K. Junge, M. Beller, J. Am. Chem. Soc. 2010, 132, 1770; 13cS. Das, S. Zhou, D. Addis, S. Enthaler, K. Junge, M. Beller, Top. Catal. 2010, 53, 979. 14For TBAF-catalyzed hydrosilylations of ketones, see: 14aJ. Boyer, R. J. P. Corriu, R. Perz, C. Reye, Tetrahedron 1981, 37, 2165; 14bM. Fujita, T. Hiyama, J. Am. Chem. Soc. 1984, 106, 4629; 14cM. Fujita, T. Hiyama, J. Am. Chem. Soc. 1985, 107, 8294; 14dD. Yang, D. D. Tanner, J. Org. Chem. 1986, 51, 2267; 14eM. Fujita, T. Hiyama, J. Org. Chem. 1988, 53, 5405; 14fM. D. Drew, N. J. Lawrence, D. Fontaine, L. Sekhri, Synlett 1997, 989; 14gM. D. Drew, N. J. Lawrence, Tetrahedron Lett. 1997, 38, 5857; 14hY. Kobayashi, E. Takahashi, M. Nakano, K. Watatani, Tetrahedron 1997, 53, 1627. 15For a review on the use of PMHS, see: N. J. Lawrence, M. D. Drew, S. M. Bushell, J. Chem. Soc. Perkin Trans. 1 1999, 3381. 16W. Flitsch, Chem. Berichte 1961, 94, 2494. 17G. Socrates, Infrared and Raman characteristic group frequencies, Wiley, Chichester, 2001, pp. 241–246. 18For mechanistic studies of the reaction of fluoride with silanes, see: 18aJ. Boyer, R. J. P. Corriu, R. Perz, C. Reye, Tetrahedron 1981, 37, 2165; 18bR. J. O. Corriu, R. Perz, C. Reye, Tetrahedron 1983, 39, 999; 18cD. Yang, D. D. Tanner, J. Org. Chem. 1986, 51, 2267; 18dC. Chult, R. J. P. Corriu, C. Reye, J. C. Young, Chem. Rev. 1993, 93, 1371. 19 19aN. S. Shaikh, K. Junge, M. Beller, Org. Lett. 2007, 9, 5429; 19bN. S. Shaikh, S. Enthaler, K. Junge, M. Beller, Angew. Chem. 2008, 120, 2531; Angew. Chem. Int. Ed. 2008, 47, 2497. Citing Literature Volume50, Issue39September 19, 2011Pages 9180-9184 ReferencesRelatedInformation
最长约 10秒,即可获得该文献文件

科研通智能强力驱动
Strongly Powered by AbleSci AI
更新
大幅提高文件上传限制,最高150M (2024-4-1)

科研通是完全免费的文献互助平台,具备全网最快的应助速度,最高的求助完成率。 对每一个文献求助,科研通都将尽心尽力,给求助人一个满意的交代。
实时播报
yrma完成签到,获得积分10
刚刚
那奇泡芙发布了新的文献求助10
1秒前
6秒前
zyz给zyz的求助进行了留言
6秒前
8秒前
那奇泡芙完成签到,获得积分10
9秒前
科研通AI2S应助爱听歌笑寒采纳,获得10
10秒前
11秒前
互助遵法尚德应助maaicui采纳,获得10
13秒前
luyu完成签到,获得积分10
13秒前
吃桂花的芒果完成签到,获得积分10
13秒前
苏书白应助唯有采纳,获得10
14秒前
zzz发布了新的文献求助10
16秒前
16秒前
小鱼发布了新的文献求助10
19秒前
黄阿鹏发布了新的文献求助10
19秒前
19秒前
20秒前
wzy完成签到,获得积分20
20秒前
20秒前
21秒前
22秒前
俊哥完成签到,获得积分10
23秒前
echo发布了新的文献求助10
23秒前
shufessm发布了新的文献求助10
24秒前
25秒前
25秒前
kiki发布了新的文献求助10
25秒前
wmm发布了新的文献求助10
25秒前
26秒前
26秒前
27秒前
28秒前
28秒前
库库发布了新的文献求助10
31秒前
Dayle发布了新的文献求助10
31秒前
abjz完成签到,获得积分10
32秒前
铭铭完成签到,获得积分10
33秒前
默默的阑悦完成签到,获得积分10
35秒前
Miller给iNk的求助进行了留言
35秒前
高分求助中
Evolution 10000
Sustainability in Tides Chemistry 2800
The Young builders of New china : the visit of the delegation of the WFDY to the Chinese People's Republic 1000
юрские динозавры восточного забайкалья 800
Diagnostic immunohistochemistry : theranostic and genomic applications 6th Edition 500
Chen Hansheng: China’s Last Romantic Revolutionary 500
China's Relations With Japan 1945-83: The Role of Liao Chengzhi 400
热门求助领域 (近24小时)
化学 医学 生物 材料科学 工程类 有机化学 生物化学 物理 内科学 纳米技术 计算机科学 化学工程 复合材料 基因 遗传学 催化作用 物理化学 免疫学 量子力学 细胞生物学
热门帖子
关注 科研通微信公众号,转发送积分 3149266
求助须知:如何正确求助?哪些是违规求助? 2800354
关于积分的说明 7839707
捐赠科研通 2457979
什么是DOI,文献DOI怎么找? 1308158
科研通“疑难数据库(出版商)”最低求助积分说明 628456
版权声明 601706