Base-promoted synthesis of tetrasubstituted alkenylboronates from propargyl amines and B2pin2via dual 1,4-metallate shift and B–N elimination

Liu, Kang; Jin, Shengnan; Song, Qiuling

doi:10.1039/d2qo01576e

Org. Chem. Front.

2023

DOI: 10.1039/d2qo01576e

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Base-promoted synthesis of tetrasubstituted alkenylboronates from propargyl amines and B₂pin₂via dual 1,4-metallate shift and B–N elimination

Kang Liu

Shengnan Jin

Qiuling Song

Abstract: An efficient approach to tetrasubstituted alkenylboronates via a cascade borylation/B−N elimination of propargyl amines and B2pin2 was disclosed. A series of tetrasubstituted alkenylboronates were readily furnished with this strategy in...

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Unlocking Diverse π-Bond Enrichment Frameworks by the Synthesis and Conversion of Boronated Phenyldiethynylethylenes

Xie,

Li,

et al. 2024

J. Am. Chem. Soc.

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The π-bond enrichment frameworks not only serve as a crucial building block in organic synthesis but also assume a pivotal role in the fields of materials science, biomedicine, photochemistry, and other related disciplines owing to their distinctive structural characteristics. The incorporation of various substituents into the C�C double bonds of tetrasubstituted alkenes is currently a highly significant research area. However, the synthesis of tetrasubstituted alkenes with diverse substituents on double bonds poses a significant challenge in achieving stereoselectivity. Here, we reported an efficient and convergent route of Cu-catalyzed borylalkynylation of both symmetrical and unsymmetrical 1,3-diynes, B 2 pin 2 , and acetylene bromide to the construction of boronated phenyldiethynylethylene (BPDEE) derivatives with excellent chemo-, stereo-, and regioselectivities. BPDEE derivatives could transform into novel tetrasubstituted organic πconjugated gem-diphenyldiethynylethylene (DPDEE), vinylphenyldiethynylethylene (VPDEE), and phenyltriethynylethylene (PTEE) derivatives by a stepwise process, which provides a flexible platform for the synthesis of complex π-bond enrichment frameworks that were difficult to synthesize by previous methods. The initial optical characterization revealed that the synthesized molecules exhibited aggregation-induced emission (AIE) properties, which further establishes the groundwork for future applications and enriches and advances the field of functional π-conjugated frameworks research.

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Unlocking Diverse π-Bond Enrichment Frameworks by the Synthesis and Conversion of Boronated Phenyldiethynylethylenes

Xie,

Li,

et al. 2024

J. Am. Chem. Soc.

Self Cite

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show abstract

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Base-promoted synthesis of tetrasubstituted alkenylboronates from propargyl amines and B₂pin₂via dual 1,4-metallate shift and B–N elimination

Abstract: An efficient approach to tetrasubstituted alkenylboronates via a cascade borylation/B−N elimination of propargyl amines and B2pin2 was disclosed. A series of tetrasubstituted alkenylboronates were readily furnished with this strategy in...

Cited by 1 publication

References 84 publications

Unlocking Diverse π-Bond Enrichment Frameworks by the Synthesis and Conversion of Boronated Phenyldiethynylethylenes

Unlocking Diverse π-Bond Enrichment Frameworks by the Synthesis and Conversion of Boronated Phenyldiethynylethylenes

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