Radical Cyclization of Alkene-Tethered Ketones Initiated by Hydrogen-Atom Transfer

Saladrigas Mar; Bosch Caroline; Saborit Gisela V.; Bonjoch Josep; Bradshaw Ben

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Radical Cyclization of Alkene-Tethered Ketones Initiated by Hydrogen-Atom Transfer

机译：由氢原子转移引发的烯萜酮的自由基环化

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摘要

An unprecedented C-C coupling reaction between alkenes and ketones by hydrogen-atom transfer, using Fe-(acac)(3) and PhSiH3 in EtOH, is described. This mild protocol features high site selectivity and allows the construction of sterically congested structures containing tertiary alcohols and quaternary centers. The overall process introduces a novel strategic bond disconnection for ring-closing reactions.

机译：描述了使用Fe-（ACAC）（3）和EtOH中的氢原子转移的烯烃和酮与EtOH中的前所未有的C-C偶联反应。这种温和的协议具有高位选择性，并允许构建含有叔醇和第四纪中心的空中拥挤结构。整体过程介绍了一种用于闭环反应的新型战略粘合断线。

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来源
《Angewandte Chemie》 |2018年第1期|共5页
作者
Saladrigas Mar; Bosch Caroline; Saborit Gisela V.; Bonjoch Josep; Bradshaw Ben;
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作者单位

Univ Barcelona IBUB Fac Farm Lab Quim Organ Av Joan 23 S-N E-08028 Barcelona Spain;

Univ Barcelona IBUB Fac Farm Lab Quim Organ Av Joan 23 S-N E-08028 Barcelona Spain;

Univ Barcelona IBUB Fac Farm Lab Quim Organ Av Joan 23 S-N E-08028 Barcelona Spain;

Univ Barcelona IBUB Fac Farm Lab Quim Organ Av Joan 23 S-N E-08028 Barcelona Spain;

Univ Barcelona IBUB Fac Farm Lab Quim Organ Av Joan 23 S-N E-08028 Barcelona Spain;

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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
alkenes; cyclizations; iron; ketones; radicals;

机译：alkenes;环化;铁;ketones;自由基;

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专利

1. Radical Cyclization of Alkene-Tethered Ketones Initiated by Hydrogen-Atom Transfer [J] . Saladrigas Mar, Bosch Caroline, Saborit Gisela V., Angewandte Chemie . 2018,第1期

机译：由氢原子转移引发的烯萜酮的自由基环化
2. Tandem transfer hydrogenation-epoxidation of ketone substrates catalysed by alkene-tethered Ru(ii)-NHC complexes [J] . Malan Frederick P., Singleton Eric, van Rooyen Petrus H., New Journal of Chemistry . 2019,第22期

机译：串联转移氢化氢化 - 环氧化烯酮（II）-NHC复合物催化的酮基材
3. Synthesis of (±)-gymnomitrol. Mn(Oac)3-initiated free-radical cyclization of alkynyl ketones [J] . Steven V.ONeil, Cheri A.Quickley, Barry B.Snider The Journal of Organic Chemistry . 1997,第7期

机译：（±）-gymnomitrol的合成。 Mn（Oac）3引发的炔酮自由基环化
4. MODELING OF REVERSE ATOM TRANSFER RADICAL POLYMERIZATION IN MINIEMULSION INITIATED BY A WATER-SOLUBLE RADICAL INITIATOR [C] . Ayelen Zurman, Mariano Asteasuain, Claudia Sarmoria AIChE Annual Meeting . 2016

机译：水溶性自由基引发剂引发逆原子转移自由基聚合的建模
5. Measurements of the kinetics of the hydroxyl radical-initiated oxidation of isoprene, methyl vinyl ketone, and methacrolein. [D] . Chuong, Bao. 2002

机译：异戊二烯，甲基乙烯基酮和甲基丙烯醛的羟基自由基引发的氧化动力学的测量。
6. Palladium-Catalyzed Atom-Transfer Radical Cyclization at Remote Unactivated C(sp3)–H Sites: Hydrogen-Atom Transfer of Hybrid Vinyl Palladium Radical Intermediates [O] . Maxim Ratushnyy, Marvin Parasram, Yang Wang, -1

机译：远端未活化的C（sp3）–H位置处的钯催化原子转移自由基环化：杂化乙烯基钯自由基中间体的氢原子转移
7. Radical Cations in Synthesis: Utilizing an Electron Transfer-Initiated Cyclization Toward the Natural Product Apicularen A [O] . Poniatowski Alexander James 2009

机译：合成中的自由基阳离子：利用电子转移引发的环向天然产物Apicularen A的转移
8. Living/Controlled Radical Polymerization. Transition-Metal-Catalyzed AtomTransfer Radical Polymerization in the Presence of a Conventional Radical Initiator [R] . Wang, J. S., Matyjaszewski, K. 1995

机译：活性/可控自由基聚合。在常规自由基引发剂存在下的过渡金属催化的原子转移自由基聚合

Radical Cyclization of Alkene-Tethered Ketones Initiated by Hydrogen-Atom Transfer

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