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Literature DB >> 23113557

Direct catalytic anti-markovnikov hydroetherification of alkenols.

Abstract

A direct intramolecular anti-Markovnikov hydroetherification reaction of alkenols is described. By employing catalytic quantities of commercially available 9-mesityl-10-methylacridinium perchlorate and 2-phenylmalononitrile as a redox-cycling source of a H-atom, we report the anti-Markovnikov hydroetherification of alkenes with complete regioselectivity. In addition, we present results demonstrating that this novel catalytic system can be applied to the anti-Markovnikov hydrolactonization of alkenoic acids.

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Year: 2012 PMID： 23113557 PMCID： PMC3513336 DOI： 10.1021/ja309635w

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

16 in total

1. Anti-Markovnikov hydrofunctionalization of olefins mediated by rhodium-porphyrin complexes.

Authors: Melanie S Sanford; John T Groves
Journal: Angew Chem Int Ed Engl Date: 2004-02-01 Impact factor: 15.336

2. Electron-transfer state of 9-mesityl-10-methylacridinium ion with a much longer lifetime and higher energy than that of the natural photosynthetic reaction center.

Authors: Shunichi Fukuzumi; Hiroaki Kotani; Kei Ohkubo; Seiji Ogo; Nikolai V Tkachenko; Helge Lemmetyinen
Journal: J Am Chem Soc Date: 2004-02-18 Impact factor: 15.419

3. Visible light photoredox catalysis: applications in organic synthesis.

Authors: Jagan M R Narayanam; Corey R J Stephenson
Journal: Chem Soc Rev Date: 2010-06-08 Impact factor: 54.564

4. Visible light photocatalysis as a greener approach to photochemical synthesis.

Authors: Tehshik P Yoon; Michael A Ischay; Juana Du
Journal: Nat Chem Date: 2010-06-23 Impact factor: 24.427

5. Intramolecular hydroalkoxylation in Brønsted acidic ionic liquids and its application to the synthesis of (±)-centrolobine.

Authors: Yunkyung Jeong; Do-Young Kim; Yunsil Choi; Jae-Sang Ryu
Journal: Org Biomol Chem Date: 2010-11-15 Impact factor: 3.876

Review 6. Hydroamination: direct addition of amines to alkenes and alkynes.

Authors: Thomas E Müller; Kai C Hultzsch; Miguel Yus; Francisco Foubelo; Mizuki Tada
Journal: Chem Rev Date: 2008-08-26 Impact factor: 60.622

7. Stereochemical memory effects in alkene radical cation/anion contact ion pairs: effect of substituents, and models for diastereoselectivity.

Authors: David Crich; Krishnakumar Ranganathan
Journal: J Am Chem Soc Date: 2005-07-13 Impact factor: 15.419

8. Efficient photocatalytic oxygenation of aromatic alkene to 1,2-dioxetane with oxygen via electron transfer.

Authors: Kei Ohkubo; Takashi Nanjo; Shunichi Fukuzumi
Journal: Org Lett Date: 2005-09-15 Impact factor: 6.005

9. Rhodium-catalyzed anti-Markovnikov hydroamination of vinylarenes.

Authors: Masaru Utsunomiya; Ryoichi Kuwano; Motoi Kawatsura; John F Hartwig
Journal: J Am Chem Soc Date: 2003-05-14 Impact factor: 15.419

10. Tandem polar/radical crossover sequences for the formation of fused and bridged bicyclic nitrogen heterocycles involving radical ionic chain reactions, and alkene radical cation intermediates, performed under reducing conditions: scope and limitations.

Authors: David Crich; Krishnakumar Ranganathan; Santhosh Neelamkavil; Xianhai Huang
Journal: J Am Chem Soc Date: 2003-07-02 Impact factor: 15.419

56 in total

1. Temporal separation of catalytic activities allows anti-Markovnikov reductive functionalization of terminal alkynes.

Authors: Le Li; Seth B Herzon
Journal: Nat Chem Date: 2013-11-17 Impact factor: 24.427

2. Photocatalytic Oxyamination of Alkenes: Copper(II) Salts as Terminal Oxidants in Photoredox Catalysis.

Authors: Nicholas L Reed; Madeline I Herman; Vladimir P Miltchev; Tehshik P Yoon
Journal: Org Lett Date: 2018-11-08 Impact factor: 6.005

3. Organic Photoredox Catalysis as a General Strategy for Anti-Markovnikov Alkene Hydrofunctionalization.

Authors: David A Nicewicz; David S Hamilton
Journal: Synlett Date: 2014-03-05 Impact factor: 2.454

4. anti-Markovnikov hydroamination of alkenes catalyzed by a two-component organic photoredox system: direct access to phenethylamine derivatives.

Authors: Tien M Nguyen; Namita Manohar; David A Nicewicz
Journal: Angew Chem Int Ed Engl Date: 2014-04-24 Impact factor: 15.336

5. Catalysis: dual catalysis at the flick of a switch.

Authors: James J Devery; Corey R J Stephenson
Journal: Nature Date: 2015-03-05 Impact factor: 49.962

6. Reversing the Regioselectivity of Halofunctionalization Reactions through Cooperative Photoredox and Copper Catalysis.

Authors: Jeremy D Griffin; Cortney L Cavanaugh; David A Nicewicz
Journal: Angew Chem Int Ed Engl Date: 2017-01-20 Impact factor: 15.336