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Literature DB >> 27159831

Nickel-Catalyzed Intramolecular C-O Bond Formation: Synthesis of Cyclic Enol Ethers.

Seo-Jung Han¹, Ryohei Doi¹, Brian M Stoltz².

Abstract

An efficient and exceptionally mild intramolecular nickel-catalyzed carbon-oxygen bond-forming reaction between vinyl halides and primary, secondary, and tertiary alcohols has been achieved. Zinc powder was found to be an essential additive for obtaining high catalyst turnover and yields. This operationally simple method allows direct access to cyclic vinyl ethers in high yields in a single step.

Entities: Chemical Gene Species

Keywords: alcohols; cross-coupling; ethers; heterocycles; nickel

Mesh：

Substances：

Year: 2016 PMID： 27159831 PMCID： PMC4985346 DOI： 10.1002/anie.201601991

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

23 in total

1. Nickel Catalysis: Synergy between Method Development and Total Synthesis.

Authors: Eric A Standley; Sarah Z Tasker; Kim L Jensen; Timothy F Jamison
Journal: Acc Chem Res Date: 2015-04-23 Impact factor: 22.384

Review 2. Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners.

Authors: Ranjan Jana; Tejas P Pathak; Matthew S Sigman
Journal: Chem Rev Date: 2011-02-14 Impact factor: 60.622

3. Copper-assisted nickel catalyzed ligand-free C(sp2)-O cross-coupling of vinyl halides and phenols.

Authors: Debasish Kundu; Pintu Maity; Brindaban C Ranu
Journal: Org Lett Date: 2014-02-06 Impact factor: 6.005

4. Efficient ring-closing metathesis of alkenyl bromides: the importance of protecting the catalyst during the olefin approach.

Authors: Michele Gatti; Emma Drinkel; Linglin Wu; Ivano Pusterla; Fiona Gaggia; Reto Dorta
Journal: J Am Chem Soc Date: 2010-11-03 Impact factor: 15.419

5. Fe/Cr- and Co/Cr-mediated catalytic asymmetric 2-haloallylations of aldehydes.

Authors: Michio Kurosu; Mei-Huey Lin; Yoshito Kishi
Journal: J Am Chem Soc Date: 2004-10-06 Impact factor: 15.419

6. Copper(I)-catalyzed aryl bromides to form intermolecular and intramolecular carbon-oxygen bonds.

Authors: Jiajia Niu; Pengran Guo; Juntao Kang; Zhigang Li; Jingwei Xu; Shaojing Hu
Journal: J Org Chem Date: 2009-07-17 Impact factor: 4.354

7. Copper-promoted coupling of vinyl boronates and alcohols: a mild synthesis of allyl vinyl ethers.

Authors: Ryan E Shade; Alan M Hyde; John-Carl Olsen; Craig A Merlic
Journal: J Am Chem Soc Date: 2010-02-03 Impact factor: 15.419

8. Transition-metal-catalyzed Suzuki-Miyaura cross-coupling reactions: a remarkable advance from palladium to nickel catalysts.

Authors: Fu-She Han
Journal: Chem Soc Rev Date: 2013-06-21 Impact factor: 54.564

Nickel-Catalyzed Intramolecular C-O Bond Formation: Synthesis of Cyclic Enol Ethers.

1. Nickel Catalysis: Synergy between Method Development and Total Synthesis.

Review 2. Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners.

3. Copper-assisted nickel catalyzed ligand-free C(sp2)-O cross-coupling of vinyl halides and phenols.

4. Efficient ring-closing metathesis of alkenyl bromides: the importance of protecting the catalyst during the olefin approach.

5. Fe/Cr- and Co/Cr-mediated catalytic asymmetric 2-haloallylations of aldehydes.

6. Copper(I)-catalyzed aryl bromides to form intermolecular and intramolecular carbon-oxygen bonds.

7. Copper-promoted coupling of vinyl boronates and alcohols: a mild synthesis of allyl vinyl ethers.

8. Transition-metal-catalyzed Suzuki-Miyaura cross-coupling reactions: a remarkable advance from palladium to nickel catalysts.

Review 9. Recent advances in homogeneous nickel catalysis.

10. Switching on elusive organometallic mechanisms with photoredox catalysis.

1. Copper-Catalyzed Enantioselective Allylic Alkylation with a γ-Butyrolactone-Derived Silyl Ketene Acetal.

2. Identifying the Imperative Role of Metal-Olefin Interactions in Catalytic C-O Reductive Elimination from Nickel(II).

3. A Synthetic Strategy toward Eight-Membered Cyclic Amines by Cycloetherification and Claisen Rearrangement.

4. Regioselectivity Influences in Platinum-Catalyzed Intramolecular Alkyne O-H and N-H Additions.

5. A C-to-O atom-swapping reaction sequence enabled by Ni-catalyzed decarbonylation of lactones.

6. Dialkyl Ether Formation at High-Valent Nickel.