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Literature DB >> 19123833

An efficient synthesis of terminal allenes from terminal 1-alkynes.

Abstract

We have developed a modified method for the synthesis of terminal allenes from terminal 1-alkyne: The reaction of 1-alkynes with 1.8 equiv of Cy(2)NH and 2.5 equiv of paraformaldehyde mediated by CuI (0.5 equiv) in refluxing dioxane may produce terminal allenes in much higher yields than the previously reported protocol and many functional groups such as mesylate, hydroxyl group, ether, amide, etc. may be tolerated.

Entities: Chemical

Year: 2009 PMID： 19123833 DOI： 10.1021/jo802391x

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

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Cited

9 in total

1. A Catalytic Approach for Enantioselective Synthesis of Homoallylic Alcohols Bearing a Z-Alkenyl Chloride or Trifluoromethyl Group. A Concise and Protecting Group-Free Synthesis of Mycothiazole.

Authors: Ryan J Morrison; Farid W van der Mei; Filippo Romiti; Amir H Hoveyda
Journal: J Am Chem Soc Date: 2019-12-24 Impact factor: 15.419

2. Regiodivergent and Diastereoselective CuH-Catalyzed Allylation of Imines with Terminal Allenes.

Authors: Richard Y Liu; Yang Yang; Stephen L Buchwald
Journal: Angew Chem Int Ed Engl Date: 2016-10-10 Impact factor: 15.336

3. Iron-Catalyzed Contrasteric Functionalization of Allenic C(sp²)-H Bonds: Synthesis of α-Aminoalkyl 1,1-Disubstituted Allenes.

Authors: Yidong Wang; Sarah G Scrivener; Xiao-Dong Zuo; Ruihan Wang; Philip N Palermo; Ethan Murphy; Austin C Durham; Yi-Ming Wang
Journal: J Am Chem Soc Date: 2021-09-07 Impact factor: 16.383

9. Synthesis of Propargylamines via Michael Addition Using Methyl Vinyl Ketone Derivatives, 1-Alkynes, and Secondary Amines Catalyzed by Copper (I) Halides.

Authors: Bantu Udaykumar; Mariappan Periasamy
Journal: ACS Omega Date: 2019-12-02

9 in total

An efficient synthesis of terminal allenes from terminal 1-alkynes.

1. A Catalytic Approach for Enantioselective Synthesis of Homoallylic Alcohols Bearing a Z-Alkenyl Chloride or Trifluoromethyl Group. A Concise and Protecting Group-Free Synthesis of Mycothiazole.

2. Regiodivergent and Diastereoselective CuH-Catalyzed Allylation of Imines with Terminal Allenes.

3. Iron-Catalyzed Contrasteric Functionalization of Allenic C(sp²)-H Bonds: Synthesis of α-Aminoalkyl 1,1-Disubstituted Allenes.

4. Generation of α-Boryl Radicals by H^. Transfer and their Use in Cycloisomerizations.

5. Gold Catalysis-Facilitated Rapid Synthesis of the Daphnane/Tigliane Tricyclic Core.

6. Borane-induced ring closure reaction of oligomethylene-linked bis-allenes.

7. Halogenoborane mediated allene cyclooligomerization.

8. Gold-catalyzed oxycyclization of allenic carbamates: expeditious synthesis of 1,3-oxazin-2-ones.

9. Synthesis of Propargylamines via Michael Addition Using Methyl Vinyl Ketone Derivatives, 1-Alkynes, and Secondary Amines Catalyzed by Copper (I) Halides.