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Literature DB >> 29657365

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

Abstract

The development of a general catalyst system for the direct anti-Markovnikov hydrofunctionalization of alkenes is presented. A unique catalyst system comprised of an acridinium photooxidant and a hydrogen atom transfer reagent allows for a range of alkene anti-Markovnikov hydrofunctionalization reactions including hydroalkoxylation, hydroamination, and hydroacetoxylation.

Entities: Chemical Species

Keywords: alkenes; hydroalkoxylation; hydroamination; organocatalysis; photoredox

Year: 2014 PMID： 29657365 PMCID： PMC5895094 DOI： 10.1055/s-0033-1340738

Source DB: PubMed Journal: Synlett ISSN： 0936-5214 Impact factor: 2.454

33 in total

1. 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

2. Misleading effects of impurities derived from the extremely long-lived electron-transfer state of 9-mesityl-10-methylacridinium ion.

Authors: Kei Ohkubo; Hiroaki Kotani; Shunichi Fukuzumi
Journal: Chem Commun (Camb) Date: 2005-07-01 Impact factor: 6.222

3. Charge shift and triplet state formation in the 9-mesityl-10-methylacridinium cation.

Authors: Andrew C Benniston; Anthony Harriman; Peiyi Li; James P Rostron; Hendrik J van Ramesdonk; Michiel M Groeneveld; Hong Zhang; Jan W Verhoeven
Journal: J Am Chem Soc Date: 2005-11-23 Impact factor: 15.419

Review 4. 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

Review 5. The economies of synthesis.

Authors: Timothy Newhouse; Phil S Baran; Reinhard W Hoffmann
Journal: Chem Soc Rev Date: 2009-08-21 Impact factor: 54.564

Review 6. Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis.

Authors: Christopher K Prier; Danica A Rankic; David W C MacMillan
Journal: Chem Rev Date: 2013-03-19 Impact factor: 60.622

7. Direct catalytic anti-Markovnikov addition of carboxylic acids to alkenes.

Authors: Andrew J Perkowski; David A Nicewicz
Journal: J Am Chem Soc Date: 2013-07-03 Impact factor: 15.419

8. Illumination of the 9-mesityl-10-methylacridinium ion does not give a long-lived photoredox state.

Authors: Andrew C Benniston; Anthony Harriman; Peiyi Li; James P Rostron; Jan W Verhoeven
Journal: Chem Commun (Camb) Date: 2005-04-08 Impact factor: 6.222

9. Anti-Markovnikov hydroamination of alkenes catalyzed by an organic photoredox system.

Authors: Tien M Nguyen; David A Nicewicz
Journal: J Am Chem Soc Date: 2013-06-19 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

6 in total

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

1. 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.

2. Misleading effects of impurities derived from the extremely long-lived electron-transfer state of 9-mesityl-10-methylacridinium ion.

3. Charge shift and triplet state formation in the 9-mesityl-10-methylacridinium cation.

Review 4. Hydroamination: direct addition of amines to alkenes and alkynes.

Review 5. The economies of synthesis.

Review 6. Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis.

7. Direct catalytic anti-Markovnikov addition of carboxylic acids to alkenes.

8. Illumination of the 9-mesityl-10-methylacridinium ion does not give a long-lived photoredox state.

9. Anti-Markovnikov hydroamination of alkenes catalyzed by an organic photoredox system.

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.

1. Anti-Markovnikov Hydroazidation of Activated Olefins via Organic Photoredox Catalysis.

2. Three-Component Olefin Dicarbofunctionalization Enabled by Nickel/Photoredox Dual Catalysis.

3. Synthesis of Chiral Tetrahydrofurans and Pyrrolidines by Visible-Light-Mediated Deoxygenation.

4. Photo-Organocatalytic Enantioselective Radical Cascade Reactions of Unactivated Olefins.

5. Metal-free visible light photoredox enables generation of carbyne equivalents via phosphonium ylide C-H activation.

6. Photocatalytic Umpolung of N- and O-substituted alkenes for the synthesis of 1,2-amino alcohols and diols.