Your browser doesn't support javascript.
loading
Unveiling Hetero-Enyne Reactivity of Aryliminoboranes: Dearomative Hetero-Diels-Alder-Like Reactions.
Qiu, Shuang; Zhang, Xin; Hu, Chaopeng; Chu, Hongxu; Li, Qianli; Ruiz, David A; Liu, Liu Leo; Tung, Chen-Ho; Kong, Lingbing.
Affiliation
  • Qiu S; School of Chemistry and Chemical Engineering, Shandong University, Jinan, 250100, China.
  • Zhang X; Department of Chemistry, Shenzhen Grubbs Institute and Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, 518055, China.
  • Hu C; Department of Chemistry, Shenzhen Grubbs Institute and Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, 518055, China.
  • Chu H; School of Chemistry and Chemical Engineering, Shandong University, Jinan, 250100, China.
  • Li Q; School of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng, 252059, China.
  • Ruiz DA; Department of Chemistry, Shenzhen Grubbs Institute and Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, 518055, China.
  • Liu LL; Department of Chemistry, Shenzhen Grubbs Institute and Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, 518055, China.
  • Tung CH; School of Chemistry and Chemical Engineering, Shandong University, Jinan, 250100, China.
  • Kong L; School of Chemistry and Chemical Engineering, Shandong University, Jinan, 250100, China.
Angew Chem Int Ed Engl ; 61(34): e202205814, 2022 Aug 22.
Article in En | MEDLINE | ID: mdl-35713957
ABSTRACT
Being isoelectronic with alkynes, iminoboranes with a polar B≡N triple bond have been exclusively investigated as a potent 1,2-dipole in synthetic chemistry. Herein, we disclose the unprecedented reactivity of aryliminoboranes via the BNCC π conjugation, namely hetero-enyne behavior. This allows for facile dearomative Diels-Alder-like reactions of aryliminoboranes with aldehydes. This cycloaddition features mild conditions, is catalyst-free, and has a broad substrate scope and good functional group tolerance. Kinetic and computational studies reveal its second-order reaction and concerted cyclization mechanism. This report unveils new synthetic application of iminoboranes beyond their classical reaction patterns.
Key words
Fulltext
Add to My VHL
Print
XML
PubMed Links
Search on Google

Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Angew Chem Int Ed Engl Year: 2022 Document type: Article Affiliation country: China
Fulltext
Add to My VHL
Print
XML
PubMed Links
Search on Google

Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Angew Chem Int Ed Engl Year: 2022 Document type: Article Affiliation country: China