Highly efficient asymmetric aerobic oxidative coupling of 2-naphthols in the presence of bioinspired iron aminopyridine complexes

Nikolay V. Tkachenko; Oleg Y. Lyakin; Denis G. Samsonenko; Evgenii P. Talsi; Konstantin P. Bryliakov

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Highly efficient asymmetric aerobic oxidative coupling of 2-naphthols in the presence of bioinspired iron aminopyridine complexes

机译：在生物悬浮铁氨基吡啶配合物存在下，高效的不对称有氧氧化偶联2-萘酚

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Abstract

For the first time, it has been shown that chiral bipyrrolidine derived bioinspired non-heme iron complexes of the types [LFeX2], [LFe(μ-O)2FeL][X]4, and [LFe(μ-O)(μ-OAc)FeL][X]2(where L – aminopyridine ligand, X?=OTf?, SbF6?, ClO4?) are capable of efficiently conducting aerobic oxidative coupling of 2-naphthols in an asymmetric fashion, with formation of the corresponding enantiomerically enriched BINOLs (up to 56%ee) in good yields (up to 94% within 24h), using as little as 1mol% of the catalyst. The effect of ligand substitutents, solvent, counteranion, 2-naphthol structure, and oxygen pressure on the catalytic performance has been systematically examined.

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Highlights

?Bioinspired Fe complexes catalyze the aerobic oxidative coupling of 2-naphthols with up to 56%ee.

?The catalysts demonstrate unprecedented high activities and efficiencies.

?A rare example of oxidase (rather than oxygenase) activity of non-heme Fe complexes is presented.

?Preliminary kinetic and mechanistic data are discussed.

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机译：摘要首次表明，手性双吡咯烷衍生的生物激发的非血红素铁络合物类型为[LFeX2]，[LFe（-O））2.2FeL[X][X]μμCE22[ce:inf>2[ce[ce:inf[[[[[[ce:inf:inf>2.infFEFE2[[[[ce>2.inf>FEFEFEFEFEFE2]FEFEFE[[[[[2.CE2.CE2.inf>ce>ce[[[[[[[[ce:inf:inf>ce>ce>ce>CE2.inf>ce>FEFEFE[[[[[[[[[[[[[[[[[[ce:inf:inf:INFce:sup-loc=“post”>？）能够以不对称的方式有效地进行2-萘酚的好氧氧化偶联，以良好的产率（在24小时内高达94%）形成相应的对映体富集的二元醇（高达56%ee），只需使用1mol%的催化剂。系统考察了配体取代基、溶剂、反阴离子、2-萘酚结构和氧压对催化剂性能的影响图形摘要显示省略

？“>生物激发的铁络合物催化2-萘酚与高达56%ee？催化剂表现出前所未有的高活性和效率。/ce:list item>？讨论了初步的动力学和机械数据。

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来源
《Catalysis Communications》 |2018年第2018期|共6页
作者
Nikolay V. Tkachenko; Oleg Y. Lyakin; Denis G. Samsonenko; Evgenii P. Talsi; Konstantin P. Bryliakov;
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作者单位

Novosibirsk State University;

Novosibirsk State University;

Novosibirsk State University;

Novosibirsk State University;

Novosibirsk State University;

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原文格式 PDF
正文语种 eng
中图分类物理化学（理论化学）、化学物理学;
关键词
Asymmetric catalysis; C–H activation; C–C bond formation; Dioxygen; Enzyme models; Iron;

机译：不对称催化;C-H激活;C-C键形成;Dioxygen;酶模型;铁;

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专利

1. A Novel and Efficient Catalytic System for Aerobic Oxidative Coupling of 2-Naphthol Derivatives [J] . Li CHEN, Jing Bo LAN, Zhi Hua MAO, 中国化学快报（英文版） . 2004,第008期
2. Catalytic Asymmetric Coupling of 2-Naphthols by Chiral Tridentate Oxovanadium(IV) Complexes [J] . 高等学校化学研究（英文版） . 2001,第003期
3. Catalytic Asymmetric Coupling of 2-Naphthols by Chiral Tridentate Oxovanadium(IV) Complexes [J] . HON, Sang-Wen 高等学校化学研究：英文版 . 2001,第0z1期
4. Catalytic Asymmetric Coupling of 2-Naphthols by Chiral Tridentate Oxovanadium(IV) Complexes [J] . HON Sang-Wen, LI Chun-Hsin, KUO Jen-Huang, 高等学校化学研究（英文版） . 2001,第0z1期
5. Ferric hydrogensulfate catalyzed aerobic oxidative coupling of 2-naphthols in water or under solvent free conditions [J] . Hossein Eshghi, Mehdi Bakavoli, Hassanali Moradi 中国化学快报（英文版） . 2009,第006期
6. Highly efficient asymmetric aerobic oxidative coupling of 2-naphthols in the presence of bioinspired iron aminopyridine complexes [J] . Nikolay V. Tkachenko, Oleg Y. Lyakin, Denis G. Samsonenko, Catalysis Communications . 2018,第期

机译：在生物悬浮铁氨基吡啶配合物存在下，高效的非对称性氧化偶联2-萘酚
7. Iron-Catalyzed Asymmetric Aerobic Oxidation: Oxidative Coupling of 2-Naphthols [J] . Hiromichi Egami, Tsutomu Katsuki Journal of the American Chemical Society . 2009,第17期

机译：铁催化的不对称有氧氧化：2-萘酚的氧化偶联。
8. What factors influence the catalytic activity of iron-salan complexes for aerobic oxidative coupling of 2-naphthols? [J] . Kenji Matsumoto, Hiromichi Egami, Takuya Oguma, Chemical Communications . 2012,第47期

机译：哪些因素影响铁-铝配合物对2-萘的需氧氧化偶联的催化活性？
9. Catalytic Asymmetric Couplings of 2-Naphthols by Chiral Oxovanadium(Ⅳ) Complexes [C] . Sang-Weng Hon The Sixth international symposium for Chinese organic chemists . 2000

机译：手性氧钒（Ⅳ）配合物催化2-萘酚的不对称偶联
10. Progress toward the asymmetric total synthesis of chaetoglobin a selective oxidative homo- and cross-coupling of phenols using aerobic catalysts. [D] . Torruellas-Pagan, Carilyn. 2014

机译：使用好氧催化剂对酚红蛋白进行不对称全合成的进展，即酚的选择性氧化均相和交叉偶联。
11. Enantioselective Iron/Bisquinolyldiamine Ligand-Catalyzed Oxidative Coupling Reaction of 2-Naphthols [O] . Lin-Yang Wu, Muhammad Usman, Wen-Bo Liu 2020

机译：对映选择性铁/双喹啉基二胺配体催化的2-萘酚的氧化偶联反应
12. Highly Enantioselective Oxidative Couplings of 2-Naphthols Catalyzed by Chiral Bimetallic Oxovanadium Complexes with Either Oxygen or Air as Oxidant [O] . -1

机译：由手性双金属氧化钒配合物催化的2-萘酚的高映射氧化偶联，其氧气或空气作为氧化剂
13. Combination Sorbent and Reactive Chemistries for Use in Highly Efficient Aerobic Oxidations (W911NF0510081) [R] . Gagne, M. R. 2009

机译：用于高效有氧氧化的组合吸附剂和反应性化学品（W911NF0510081）

Highly efficient asymmetric aerobic oxidative coupling of 2-naphthols in the presence of bioinspired iron aminopyridine complexes

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