Aliphatic C-C Bond Cleavage in a-Hydroxy Ketones by a Dioxygen-Derived Nucleophilic Iron-Oxygen Oxidant

Shrabanti Bhattacharya; Rubina Rahaman; Sayanti Chatterjee; Tapan K. Paine

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Aliphatic C-C Bond Cleavage in a-Hydroxy Ketones by a Dioxygen-Derived Nucleophilic Iron-Oxygen Oxidant

机译：通过二恶英衍生的亲核铁 - 氧氧化剂在A-羟基酮中切割脂族C-C粘合

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摘要

A nucleophilic iron-oxygen oxidant, formed in situ in the reaction between an iron(II)-benzilate complex and O_2, oxidatively cleaves the aliphatic C-C bonds of ahydroxy ketones. In the cleavage reaction, α-hydroxy ketones without any α-C-H bond afford a 1:1 mixture of carboxylic acid and ketone. Isotope labeling studies established that one of the oxygen atoms from dioxygen is incorporated into the carboxylic acid product. Furthermore, the iron(II) complex cleaves an aliphatic C-C bond of 17- a-hydroxyprogesterone affording androstenedione and acetic acid. The O_2-dependent aliphatic C-C bond cleavage of a-hydroxy ketones containing no α-C-H bond bears similarity to the lyase activity of the heme enzyme, cytochrome P450 17A1 (CYP17A1).

机译：一种亲核铁 - 氧氧化剂，原位在铁（II） - 苯甲酸酯复合物和O_2之间的反应中形成，氧化地切割α-羟基酮的脂族C-C键。在切割反应中，没有任何α-C-H键的α-羟基酮提供1：1羧酸和酮的混合物。同位素标记研究确定，将来自二氧根的一种氧原子掺入羧酸产物中。此外，铁（II）复合物切割17-羟基戊酮的脂族C-C键，得到雄甾酮和乙酸。含有NOα-C-H键的α-羟基酮的O_2依赖性脂族C-C键裂解与血红素酶的裂解酶活性，细胞色素P450 17A1（CYP17A1）具有相似性。

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来源
《Chemistry: A European journal》 |2017年第16期|共4页
作者
Shrabanti Bhattacharya; Rubina Rahaman; Sayanti Chatterjee; Tapan K. Paine;
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作者单位

Department of Inorganic Chemistry Indian Association for the Cultivation of Science 2A &

2B Raja S. C. Mullick Road Jadavpur Kolkata 700032 (India);

Department of Inorganic Chemistry Indian Association for the Cultivation of Science 2A &

2B Raja S. C. Mullick Road Jadavpur Kolkata 700032 (India);

Department of Inorganic Chemistry Indian Association for the Cultivation of Science 2A &

2B Raja S. C. Mullick Road Jadavpur Kolkata 700032 (India);

Department of Inorganic Chemistry Indian Association for the Cultivation of Science 2A &

2B Raja S. C. Mullick Road Jadavpur Kolkata 700032 (India);

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原文格式 PDF
正文语种 eng
中图分类应用化学;
关键词
C-C bond cleavage; dioxygen; iron; nucleophilic oxidant; α-hydroxy ketones;

机译：C-C键切割;二恶英;铁;亲核氧化剂;α-羟基酮;

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1. Aliphatic C-C Bond Cleavage in a-Hydroxy Ketones by a Dioxygen-Derived Nucleophilic Iron-Oxygen Oxidant [J] . Shrabanti Bhattacharya, Rubina Rahaman, Sayanti Chatterjee, Chemistry: A European journal . 2017,第16期

机译：通过二恶英衍生的亲核铁 - 氧氧化剂在A-羟基酮中切割脂族C-C粘合
2. Olefin cis-Dihydroxylation and Aliphatic CH Bond Oxygenation by a Dioxygen-Derived Electrophilic Iron-Oxygen Oxidant [J] . Chatterjee Sayanti, Paine Tapan Kanti Angewandte Chemie . 2015,第32期

机译：双氧衍生的亲电铁氧氧化剂对烯烃的顺式-二羟基化和脂肪族CH键的氧化
3. Aliphatic C-C Bond Cleavage of alpha-Hydroxy Ketones by Non-Heme Iron(II) Complexes: Mechanistic Insight into the Reaction Catalyzed by 2,4 '-Dihydroxyacetophenone Dioxygenase [J] . Rahaman Rubina, Paria Sayantan, Paine Tapan Kanti Inorganic Chemistry: A Research Journal that Includes Bioinorganic, Catalytic, Organometallic, Solid-State, and Synthetic Chemistry and Reaction Dynamics . 2015,第22期

机译：非血红素铁（II）配合物对α-羟基酮的脂族C-C键裂解：2,4'-二羟基苯乙酮双加氧酶催化反应的机理研究
4. A Ruthenium-Catalyzed Reaction of Aromatic Ketones with Organoboronic Acid Esters:A New Method for C-C Bond Formation via C-H Bonds Cleavage [C] . Fumitoshi Kakiuchi, Shintaro Kan, Kimitaka Igi, Symposium on Organometallic Chemistry . 2003

机译：芳香酮与有机硼酸酯的芳香酮催化反应：通过C-H键切割的C-C键形成新方法
5. Catalytic C-C (C-N) Bond Formation and C-O Bond Cleavage by Pincer-Ligated Iridium Complexes [D] . Li, Bo. 2019

机译：掺杂剂铱络合物催化C-C（C-N）键合形成和C-O键切割
6. A Simple Procedure for C-C Bond Cleavage of Aromatic and Aliphatic Epoxides with Aqueous Sodium Periodate Under Ambient Conditions [O] . Caitlin M. Binder, Darryl D. Dixon, Erik Almaraz, -1

机译：在环境条件下用高碘酸钠水溶液进行芳族和脂族环氧的C-C键裂解的简单程序
7. Enantioselective synthesis of hydroxy ketones through cleavage and formation of acyloin linkage : enzymatic kinetic resolution via C-C bond cleavage [O] . Demir A. S., Pohl M., Janzen E., 2001

机译：通过裂解和形成酰胆素键的对映选择性合成羟基酮：通过C-C键裂解的酶动力学拆分

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Aliphatic C-C Bond Cleavage in a-Hydroxy Ketones by a Dioxygen-Derived Nucleophilic Iron-Oxygen Oxidant

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