B(C6F5)3-Catalyzed α,β-Difunctionalization and C–N Bond Cleavage of Saturated Amines with Benzo[c]isoxazoles: Access to Quinoline Derivatives DOI
Yan He, Qimeng Liu,

Zihe Du

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(21), P. 14840 - 14845

Published: Oct. 21, 2022

Herein, we disclose a strategy to realize α,β-difunctionalization and C–N bond cleavage of saturated amines with benzo[c]isoxazoles via B(C6F5)3-catalyzed consecutive hydrogen-borrowing [4 + 2] cycloaddition followed by process. In general, the reactions proceed efficiently in absence any oxidant metal catalyst afford broad range quinoline derivatives starting from easily accessible substrates an atom-economical manner.

Language: Английский

Recent Advances in Catalysis Using Organoborane-Mediated Hydride Abstraction DOI Creative Commons
Rebecca L. Melen, Louis C. Morrill, Alexander P. Pulis

et al.

Synlett, Journal Year: 2023, Volume and Issue: 34(18), P. 2117 - 2128

Published: June 16, 2023

Abstract C–H functionalization is widely regarded as an important area in the development of synthetic methodology, enabling design more time- and atom-efficient syntheses. The ability electron-deficient organoboranes to mediate hydride abstraction from α-amino bonds therefore great interest, reactive iminium hydridoborate moieties generated are able participate a range synthetically useful transformations. In this review, we cover recent advances made organoborane-mediated abstraction, focus on catalytic applications boranes α- or β-functionalization, α,β-difunctionalization, dehydrogenation amines. 1 Introduction 2 α-Functionalization Amines 3 β-Functionalization 4 α,β-Difunctionalization 5 Dehydrogenation 6 Summary Future Prospects

Language: Английский

Citations

6
B(C6F5)3-catalyzed stepwise 1,5-hydride migration/cyclization: diastereoselective construction of carbocyclic β-amino acid derivatives DOI
Zhiting Wang, Hongchi Liu,

Tianxiao Jiang

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 11(3), P. 864 - 870

Published: Dec. 11, 2023

A stepwise 1,5-hydride migration/cyclization reaction enabled by B(C 6 F 5 ) 3 is established to deliver the corresponding six-membered carbocyclic β-amino acid derivatives with complete diastereoselectivity.

Language: Английский

Citations

5
Borane-catalyzed dehydrogenative C–C bond formation of indoles with N-tosylhydrazones: an experimental and computational study DOI

Dipika,

Yogesh Brijwashi Sharma, Suyash Pant

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(13), P. 3428 - 3437

Published: Jan. 1, 2022

A novel dehydrogenative C–C bond formation of indoles and N -tosylhydrazones to give di(indolyl)methanes (DIMs) has been demonstrated using tris(pentafluorophenyl)borane as a catalyst.

Language: Английский

Citations

9
Borane-catalyzed arylation of aryldiazoacetates withN,N-dialkylanilines DOI
Cheng‐Yu Chen, Jing‐Hao Zhao,

Li-Xue Xiong

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(20), P. 4101 - 4104

Published: Jan. 1, 2022

We report a catalytic Friedel–Crafts type arylation of donor–acceptor diazo compounds with aniline derivatives under metal-free and mild conditions.

Language: Английский

Citations

8
B(C6F5)3-Catalyzed α,β-Difunctionalization and C–N Bond Cleavage of Saturated Amines with Benzo[c]isoxazoles: Access to Quinoline Derivatives DOI
Yan He, Qimeng Liu,

Zihe Du

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(21), P. 14840 - 14845

Published: Oct. 21, 2022

Herein, we disclose a strategy to realize α,β-difunctionalization and C–N bond cleavage of saturated amines with benzo[c]isoxazoles via B(C6F5)3-catalyzed consecutive hydrogen-borrowing [4 + 2] cycloaddition followed by process. In general, the reactions proceed efficiently in absence any oxidant metal catalyst afford broad range quinoline derivatives starting from easily accessible substrates an atom-economical manner.

Language: Английский

Citations

7