Literature DB >> 34155203

Ni-catalyzed hydroaminoalkylation of alkynes with amines.

Wei-Wei Yao1, Ran Li1, Hao Chen1, Ming-Kai Chen1, Yu-Xin Luan2, Yi Wang3, Zhi-Xiang Yu4, Mengchun Ye5.   

Abstract

Allylic amines are versatile building blocks in organic synthesis and exist in bioactive compounds, but their synthesis via hydroaminoalkylation of alkynes with amines has been a formidable challenge. Here, we report a late transition metal Ni-catalyzed hydroaminoalkylation of alkynes with N-sulfonyl amines, providing a series of allylic amines in up to 94% yield. Double ligands of N-heterocyclic carbene (IPr) and tricyclohexylphosphine (PCy3) effectively promote the reaction.

Entities:  

Year:  2021        PMID： 34155203     DOI： 10.1038/s41467-021-24032-9

Source DB:  PubMed          Journal:  Nat Commun        ISSN： 2041-1723            Impact factor:   14.919


  25 in total

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Journal:  Chem Rev       Date:  1998-06-18       Impact factor: 60.622

2.  α-Vinylation of amides with arylacetylenes: synthesis of allylamines under metal-free conditions.

Authors:  Manman Sun; Huandong Wu; Weiliang Bao
Journal:  Org Biomol Chem       Date:  2013-11-07       Impact factor: 3.876

3.  Recent advances in organocatalytic asymmetric Morita-Baylis-Hillman/aza-Morita-Baylis-Hillman reactions.

Authors:  Yin Wei; Min Shi
Journal:  Chem Rev       Date:  2013-05-17       Impact factor: 60.622

4.  α-Functionalization of Cyclic Secondary Amines: Lewis Acid Promoted Addition of Organometallics to Transient Imines.

Authors:  Anirudra Paul; Daniel Seidel
Journal:  J Am Chem Soc       Date:  2019-05-24       Impact factor: 15.419

5.  Dimethylzinc-Initiated Radical Coupling of β-Bromostyrenes with Ethers and Amines.

Authors:  Amanda Sølvhøj; Andreas Ahlburg; Robert Madsen
Journal:  Chemistry       Date:  2015-09-17       Impact factor: 5.236

6.  Direct α-C-H bond functionalization of unprotected cyclic amines.

Authors:  Weijie Chen; Longle Ma; Anirudra Paul; Daniel Seidel
Journal:  Nat Chem       Date:  2017-11-06       Impact factor: 24.427

7.  Allylic Amines as Key Building Blocks in the Synthesis of (E)-Alkene Peptide Isosteres.

Authors:  Erin M Skoda; Gary C Davis; Peter Wipf
Journal:  Org Process Res Dev       Date:  2012       Impact factor: 3.317

8.  Photoinduced Nickel-Catalyzed Chemo- and Regioselective Hydroalkylation of Internal Alkynes with Ether and Amide α-Hetero C(sp3)-H Bonds.

Authors:  Hong-Ping Deng; Xuan-Zi Fan; Zhi-Hui Chen; Qing-Hua Xu; Jie Wu
Journal:  J Am Chem Soc       Date:  2017-09-14       Impact factor: 15.419

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Journal:  Science       Date:  1984-06-15       Impact factor: 47.728

10.  Lewis Acid Catalyzed Friedel-Crafts Alkylation of Alkenes with Trifluoropyruvates.

Authors:  Bin Xiang; Teng-Fei Xu; Liang Wu; Ren-Rong Liu; Jian-Rong Gao; Yi-Xia Jia
Journal:  J Org Chem       Date:  2016-04-07       Impact factor: 4.354
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  1 in total

1.  Stereoselective Synthesis of Tertiary Allylic Amines by Titanium-Catalyzed Hydroaminoalkylation of Alkynes with Tertiary Amines.

Authors:  Tobias Kaper; Dennis Geik; Felix Fornfeist; Marc Schmidtmann; Sven Doye
Journal:  Chemistry       Date:  2022-01-25       Impact factor: 5.020
  1 in total

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