Recent Progress in Aryne Participated Dearomatization Reactions

Yan, Qiang; Fan, Rong; Liu, Binbin; Su, Shuaisong; Wang, Bo; Yao, Tuanli; Tan, Jiajing

doi:10.6023/cjoc202009009

Cited by 12 publications

(1 citation statement)

References 12 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…2008 年, 该课题组 [54] 又报道了芳炔、仲胺和 CO 2 的三组分反应(Scheme 40), 同样以优良产率得到邻氨基苯甲酸衍生物. 此外, 该课题组 [55][56] 研究一直处于停滞状态 [58] . 近来, 随着 Kobayashi 芳炔前体的发展, 芳炔与氮杂环的反应再次引起了科学家的研究兴趣.…”

Section: 芳炔参与的氮芳基化三组分反应unclassified

Recent Progress on Arylation with Aryne through Three-Component Reaction

Chen¹,

Yang²,

Li³

et al. 2023

Chinese Journal of Organic Chemistry

View full text Add to dashboard Cite

The three component reaction has the advantages of simple operation and efficient reaction, in line with the principles of atomic economy and green environmental protection. At present, the arylation without transition metal catalyst is mainly divided into three types of as following: (1) the direct arylation, (2) the insertion of aryne into σ-bond or π-bond, and (3) the three-component reactions involving aryne. Compared with the direct arylation and the insertion of aryne into σ-bond or π-bond, the mechanism of three component reactions involving aryne is still unclear, and the published reviews are still lacking. In order to facilitate the scientific researchers to consult and understand the three-component reaction involved in aryne, the progresses in the three-component reaction involving aryne in recent years are reviewed. Keywords aryne; three component reaction; carbon and heteroatom; arylation 芳炔作为一类重要的反应活性中间体一直备受人们的关注, 其参与的反应为构建碳-碳键和碳-杂键提供了新的反应模式 [1][2][3][4][5][6] , 并且在天然产物、生物碱和药物中间体的合成中具有广泛的应用 [7] . 自 1983 年 Kobayashi 课题组 [8] 首次报道 2-(三甲基甲硅烷基)苯基三氟甲磺酸酯为苯炔前体, 在氟负离子作用下高效生成苯炔的方法以来(Scheme 1), 芳炔参与的芳基化反应推动了芳炔化学的快速发展.

show abstract

Section: 芳炔参与的氮芳基化三组分反应unclassified

Recent Progress on Arylation with Aryne through Three-Component Reaction

Chen¹,

Yang²,

Li³

et al. 2023

Chinese Journal of Organic Chemistry

View full text Add to dashboard Cite

show abstract

Formal [2+1] Cycloadditions of a Metallacyclopentadiene Unit with Alkynes: Constructing Tetracyclic Conjugated Frameworks with Bridgehead Metals

Chu

Chen

et al. 2023

Chin. J. Chem.

View full text Add to dashboard Cite

Comprehensive Summary Metallacyclopentadienes play a vital role in transition‐metal mediated and catalyzed cycloaddition reactions of alkynes. Though versatile reactions of metallacyclopentadienes with alkynes have been disclosed, [2+1] cycloadditions of metallacyclopentadienes and alkynes have never been discovered. In present work, we report the formal [2+1] cycloadditions of a metallacyclopentadiene unit with a broad scope of commercial alkynes, providing a facile strategy to construct tetracyclic conjugated compounds. The deuterated experiment indicates a metal vinylidene intermediate has been involved in [2+1] cycloaddition. Moreover, the electrophilic substitution reaction of the tetracyclic conjugated compound with the aid of density functional theory (DFT) calculated Fukui functions is investigated. These tetracyclic conjugated compounds exhibit broad absorption spectra in the whole visible region which could be employed as potential photovoltaic materials.

show abstract