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

Tris(pentafluorophenyl)borane catalyzed C–C and C–heteroatom bond formation DOI
G. Vasanth Kumar, Sourav Roy, Indranil Chatterjee

et al.

Organic & Biomolecular Chemistry, Journal Year: 2021, Volume and Issue: 19(6), P. 1230 - 1267

Published: Jan. 1, 2021

This review showcases a collective depiction on the potential utility of BCF as versatile catalyst to develop various synthetic transformations.

Language: Английский

Citations

76
C–H Bond Functionalization of Amines: A Graphical Overview of Diverse Methods DOI Creative Commons

Subhradeep Dutta,

Bowen Li,

Dillon R. L. Rickertsen

et al.

SynOpen, Journal Year: 2021, Volume and Issue: 05(03), P. 173 - 228

Published: July 1, 2021

This Graphical Review provides a concise overview of the manifold and mechanistically diverse methods that enable functionalization sp

Language: Английский

Citations

65
Recent advances in the functionalization of saturated cyclic amines DOI
Yan He, Zhi Zheng, Jintao Yang

et al.

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(16), P. 4582 - 4606

Published: Jan. 1, 2021

Functionalized cyclic amines are the essential structural moieties of numerous biologically active compounds. This review summarized most recent advances in C–H, C–N and C–C bond functionalization saturated amines.

Language: Английский

Citations

63
B(C6F5)3-Catalyzed Dehydrogenation of Pyrrolidines to Form Pyrroles DOI Creative Commons

Ana Alvarez-Montoya,

Joseph P. Gillions,

Laura Winfrey

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(7), P. 4856 - 4864

Published: March 18, 2024

Pyrroles are important N-heterocycles found in medicines and materials. The formation of pyrroles from widely accessible pyrrolidines is a potentially attractive strategy but an underdeveloped approach due to the sensitivity oxidative conditions required achieve such transformation. Herein, we report catalytic that employs commercially available B(C6F5)3 operationally simple procedure allows serve as direct synthons for pyrroles. Mechanistic studies have revealed insights into borane-catalyzed dehydrogenative processes.

Language: Английский

Citations

11
Enantioselective Synthesis of N-Alkylamines through β-Amino C–H Functionalization Promoted by Cooperative Actions of B(C6F5)3 and a Chiral Lewis Acid Co-Catalyst DOI

Yejin Chang,

Min Cao, Jessica Z. Chan

et al.

Journal of the American Chemical Society, Journal Year: 2021, Volume and Issue: 143(5), P. 2441 - 2455

Published: Jan. 29, 2021

We disclose a catalytic method for β-C(sp3)–H functionalization of N-alkylamines the synthesis enantiomerically enriched β-substituted amines, entities prevalent in pharmaceutical compounds and used to generate different families chiral catalysts. demonstrate that catalyst system comprising seemingly competitive Lewis acids, B(C6F5)3, Mg- or Sc-based complex, promotes highly enantioselective union α,β-unsaturated compounds. An array δ-amino carbonyl was synthesized under redox-neutral conditions by reaction N-alkylamine-derived enamine an electrophile activated acid co-catalyst. The utility approach is highlighted late-stage β-C–H bioactive amines. Investigations regard mechanistic nuances processes are described.

Language: Английский

Citations

55
Consecutive β,β′‐Selective C(sp3)−H Silylation of Tertiary Amines with Dihydrosilanes Catalyzed by B(C6F5)3 DOI Creative Commons
Huaquan Fang, Kaixue Xie, Sebastian Kemper

et al.

Angewandte Chemie International Edition, Journal Year: 2021, Volume and Issue: 60(15), P. 8542 - 8546

Published: Feb. 19, 2021

Tris(pentafluorophenyl)borane has been found to catalyze the two-fold C(sp

Language: Английский

Citations

44
B(C6F5)3-catalyzed β-C(sp3)–H alkylation of tertiary amines with 2-aryl-3H-indol-3-ones DOI

Changpeng Zou,

Tao Ma,

Xiu‐Xiu Qiao

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(21), P. 4393 - 4397

Published: Jan. 1, 2023

Herein, we describe a B(C 6 F 5 ) 3 -catalyzed redox-neutral β-functionalization of tertiary amines with cyclic-ketimines, achieving various 1,3-diamines containing the indolin-3-one moiety via borrowing hydrogen strategy.

Language: Английский

Citations

14
Borane/Gold(I)‐Catalyzed C−H Functionalization Reactions and Cycloaddition Reactions of Amines and α‐Alkynylenones DOI

Jun‐Jie Tian,

Wei Sun,

Rui‐Rui Li

et al.

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(35)

Published: July 4, 2022

Abstract We designed a borane/gold(I) co‐catalytic system and used it for C−H functionalization reactions cycloaddition between tertiary amines α‐alkynylenones. Both effectively incorporated furan ring into the amine.

Language: Английский

Citations

22
Deconstructive Pyridylation of Unstrained Cyclic Amines through a One-Pot Umpolung Approach DOI
Seonghyeok Hong, Byeongseok Kweon, Wooseok Lee

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(15), P. 2722 - 2727

Published: April 12, 2023

A one-pot umpolung method for the ring-opening pyridylation of unstrained cyclic amines was developed using N-amidopyridinium salts. This process involves formation electron donor-acceptor complexes between bromide and salts, ultimately leading to functionalization pyridines. protocol is compatible with a range 5- or 6-membered pyridines, thereby providing powerful synthon preparing C4-functionalized pyridines under visible-light conditions in absence an external photocatalyst.

Language: Английский

Citations

12
B(C6F5)3-Catalyzed C(sp3)–H Alkylation of Tertiary Amines with Electron-Deficient Olefins: Determinants of Site Selectivity DOI

Xin-Yue Zhou,

Yingbo Shao,

Ruiting Guo

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(10), P. 8041 - 8049

Published: May 8, 2024

The reason for the site selectivity previously reported B(C6F5)3-catalyzed C(sp3)–H alkylation of tertiary amines with electron-deficient olefins remains a mystery. appears to be governed by number electron-withdrawing groups (EWGs) on olefin: one EWG results in α-alkylation, whereas two EWGs (one each end double bond) result β-alkylation. In this study, we solved mystery and unlocked pathway β-alkylation bearing only EWG. Control experiments density functional theory calculations provided detailed picture reaction mechanism both α- Furthermore, demonstrated broad scope reaction.

Language: Английский

Citations

4