Literature DB >> 29172494

Direct Synthesis of Secondary Benzylic Alcohols Enabled by Photoredox/Ni Dual-Catalyzed Cross-Coupling.

Rauful Alam1, Gary A Molander1.   

Abstract

An operationally simple, mild, redox-neutral method for the cross-coupling of α-hydroxyalkyltrifluoroborates is reported. Utilizing an Ir photocatalyst, α-hydroxyalkyl radicals are generated from the single-electron oxidation of the trifluoroborates, and these radicals are subsequently engaged in a nickel-catalyzed C-C bond-forming reaction with aryl halides. The process is highly selective, functional group tolerant, and step economical, which allows the direct synthesis of secondary benzylic alcohol motifs.

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Year:  2017        PMID： 29172494      PMCID： PMC5732067          DOI： 10.1021/acs.joc.7b02589

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  29 in total

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Authors:  Yijin Su; Xiang Sun; Guolin Wu; Ning Jiao
Journal:  Angew Chem Int Ed Engl       Date:  2013-07-24       Impact factor: 15.336

2.  Visible-Light-Triggered Directly Reductive Arylation of Carbonyl/Iminyl Derivatives through Photocatalytic PCET.

Authors:  Ming Chen; Xinxin Zhao; Chao Yang; Wujiong Xia
Journal:  Org Lett       Date:  2017-07-11       Impact factor: 6.005

3.  Stereospecific cross-coupling of secondary organotrifluoroborates: potassium 1-(benzyloxy)alkyltrifluoroborates.

Authors:  Gary A Molander; Steven R Wisniewski
Journal:  J Am Chem Soc       Date:  2012-10-01       Impact factor: 15.419

4.  Intermolecular Radical Addition to Carbonyls Enabled by Visible Light Photoredox Initiated Hole Catalysis.

Authors:  Lena Pitzer; Frederik Sandfort; Felix Strieth-Kalthoff; Frank Glorius
Journal:  J Am Chem Soc       Date:  2017-09-21       Impact factor: 15.419

5.  Protecting group-free, selective cross-coupling of alkyltrifluoroborates with borylated aryl bromides via photoredox/nickel dual catalysis.

Authors:  Yohei Yamashita; John C Tellis; Gary A Molander
Journal:  Proc Natl Acad Sci U S A       Date:  2015-09-14       Impact factor: 11.205

6.  Single-electron transmetalation: an enabling technology for secondary alkylboron cross-coupling.

Authors:  David N Primer; Idris Karakaya; John C Tellis; Gary A Molander
Journal:  J Am Chem Soc       Date:  2015-02-04       Impact factor: 15.419

7.  Mechanistic Perspectives on Organic Photoredox Catalysis for Aromatic Substitutions.

Authors:  Michal Majek; Axel Jacobi von Wangelin
Journal:  Acc Chem Res       Date:  2016-09-26       Impact factor: 22.384

8.  Palladium-Catalyzed Enantioselective Intermolecular Coupling of Phenols and Allylic Alcohols.

Authors:  Nicholas J Race; Cristiane S Schwalm; Takayuki Nakamuro; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2016-12-01       Impact factor: 15.419

9.  Inaccessibility of beta-hydride elimination from -OH functional groups in Wacker-type oxidation.

Authors:  John A Keith; Jonas Oxgaard; William A Goddard
Journal:  J Am Chem Soc       Date:  2006-03-15       Impact factor: 15.419

Review 10.  Recent advances in homogeneous nickel catalysis.

Authors:  Sarah Z Tasker; Eric A Standley; Timothy F Jamison
Journal:  Nature       Date:  2014-05-15       Impact factor: 49.962
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  3 in total

1.  Selective Hydrogen Atom Abstraction through Induced Bond Polarization: Direct α-Arylation of Alcohols through Photoredox, HAT, and Nickel Catalysis.

Authors:  Jack Twilton; Melodie Christensen; Daniel A DiRocco; Rebecca T Ruck; Ian W Davies; David W C MacMillan
Journal:  Angew Chem Int Ed Engl       Date:  2018-04-06       Impact factor: 15.336

Review 2.  Alkyl Carbon-Carbon Bond Formation by Nickel/Photoredox Cross-Coupling.

Authors:  John A Milligan; James P Phelan; Shorouk O Badir; Gary A Molander
Journal:  Angew Chem Int Ed Engl       Date:  2019-02-27       Impact factor: 15.336

3.  β-Silyloxy Allylboronate Esters through an Aldehyde Borylation/Homologation Sequence.

Authors:  Gillian F Meyer; Maggie A Nistler; Andrey V Samoshin; Brennan D McManus; Taylor A Thane; Carl J Ferber; Gregory W O'Neil; Timothy B Clark
Journal:  Tetrahedron Lett       Date:  2020-05-29       Impact factor: 2.415
  3 in total

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