Rh(<scp>iii</scp>)-catalyzed regioselective versatile indole derivatization: delivering potential of rare β-(1<i>H</i>-indol-2-yl)-β-amino acids in one pot

Zhang, Shuaizhong; Zhang, Jinquan; Zhang, Hongbin

doi:10.1039/d3cc01289a

Chem. Commun.

2023

DOI: 10.1039/d3cc01289a

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Rh(iii)-catalyzed regioselective versatile indole derivatization: delivering potential of rare β-(1H-indol-2-yl)-β-amino acids in one pot

Shuaizhong Zhang

Jinquan Zhang

Hongbin Zhang

Abstract: Rh-catalyzed selective C–H functionalization of indole with two transformation routes were developed: an alkenylation–annulation with addition of KHSO4 and alkenylation–elimination in the presence of CsOAc to the corresponding products, respectively....

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2024

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Palladium‐Catalyzed Denitrogenative Coupling of Aryldiazonium Salts with Terminal Alkynes for the Assembly of Internal Alkynes

Guo,

Xiong

2024

Eur J Org Chem

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An N‐heterocyclic carbene palladium (NHC‐palladium)‐catalyzed denitrogenative coupling of aryldiazonium salts with terminal alkynes in ionic liquids has been accomplished. This catalytic strategy provides an effective and green synthetic protocol for the assembly of structurally diverse internal alkynes with excellent functional group compatibility and mild conditions. In the presence of 1 mol % of IMes‐Pd‐Im‐Cl2 as the catalyst, a wide range of terminal alkynes and aryldiazonium salts could be excellently tolerated. Basic ionic liquid plays a crucial role in this catalytic system, which not only acts as the green solvent, but also provides basic environment for the carbon‐carbon bond formation process. Notably, this catalytic system could be recycled up to six times and reused without significant loss of catalytic activity.

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Palladium‐Catalyzed Denitrogenative Coupling of Aryldiazonium Salts with Terminal Alkynes for the Assembly of Internal Alkynes

Guo,

Xiong

2024

Eur J Org Chem

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show abstract

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Rh(iii)-catalyzed regioselective versatile indole derivatization: delivering potential of rare β-(1H-indol-2-yl)-β-amino acids in one pot

Abstract: Rh-catalyzed selective C–H functionalization of indole with two transformation routes were developed: an alkenylation–annulation with addition of KHSO4 and alkenylation–elimination in the presence of CsOAc to the corresponding products, respectively....

Cited by 1 publication

References 30 publications

Palladium‐Catalyzed Denitrogenative Coupling of Aryldiazonium Salts with Terminal Alkynes for the Assembly of Internal Alkynes

Palladium‐Catalyzed Denitrogenative Coupling of Aryldiazonium Salts with Terminal Alkynes for the Assembly of Internal Alkynes

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