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Literature DB >> 26828116

Pyridyl Directed Catalyst-Free trans-Hydroboration of Internal Alkynes.

Kang Yuan¹, Naoya Suzuki², Soren K Mellerup¹, Xiang Wang¹, Shigehiro Yamaguchi², Suning Wang^1,3.

Abstract

We report the first examples of straightforward trans-hydroboration of internal alkynes at room temperature with 9-BBN, producing five-membered BN-heterocycles. Contrary to conventional cis-hydroboration, we demonstrate that the introduction of a pyridyl group switches the stereoselectivity of the reaction. A hydride migration mechanism has been proposed and supported by DFT calculations for the trans-hydroboration. This new hydroboration approach allows facile construction of new blue fluorescent BN-heterocyclic compounds.

Entities: Chemical

Year: 2016 PMID： 26828116 DOI： 10.1021/acs.orglett.5b03698

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

5 in total

1. Site-Selective and Stereoselective trans-Hydroboration of 1,3-Enynes Catalyzed by 1,4-Azaborine-Based Phosphine-Pd Complex.

Authors: Senmiao Xu; Yuanzhe Zhang; Bo Li; Shih-Yuan Liu
Journal: J Am Chem Soc Date: 2016-11-01 Impact factor: 15.419

Pyridyl Directed Catalyst-Free trans-Hydroboration of Internal Alkynes.

1. Site-Selective and Stereoselective trans-Hydroboration of 1,3-Enynes Catalyzed by 1,4-Azaborine-Based Phosphine-Pd Complex.

2. Design and synthesis of stable four-coordinated benzotriazole-borane with tunable fluorescence emission.

3. BCl₃ -Induced Annulative Oxo- and Thioboration for the Formation of C3-Borylated Benzofurans and Benzothiophenes.

Review 4. Emergence and Applications of Base Metals (Fe, Co, and Ni) in Hydroboration and Hydrosilylation.

5. One-Metal/Two-Ligand for Dual Activation Tandem Catalysis: Photoinduced Cu-Catalyzed Anti-hydroboration of Alkynes.

Pyridyl Directed Catalyst-Free trans-Hydroboration of Internal Alkynes.

1. Site-Selective and Stereoselective trans-Hydroboration of 1,3-Enynes Catalyzed by 1,4-Azaborine-Based Phosphine-Pd Complex.

2. Design and synthesis of stable four-coordinated benzotriazole-borane with tunable fluorescence emission.

3. BCl3 -Induced Annulative Oxo- and Thioboration for the Formation of C3-Borylated Benzofurans and Benzothiophenes.

Review 4. Emergence and Applications of Base Metals (Fe, Co, and Ni) in Hydroboration and Hydrosilylation.

5. One-Metal/Two-Ligand for Dual Activation Tandem Catalysis: Photoinduced Cu-Catalyzed Anti-hydroboration of Alkynes.

3. BCl₃ -Induced Annulative Oxo- and Thioboration for the Formation of C3-Borylated Benzofurans and Benzothiophenes.