Hydrogen-bonding-assisted redox-neutral construction of tetrahydroquinolines via hydride transfer

Xiaoyu Yang; Fangzhi Hu; Liang Wang; Lubin Xu; Shuai-Shuai Li

doi:10.1039/d0ob00521e

Z−H Bond Activation in (Di)hydrogen Bonding as a Way to Proton/Hydride Transfer and H2 Evolution

Chemistry - A European Journal ◽

10.1002/chem.201704203 ◽

2017 ◽

Vol 24 (7) ◽

pp. 1464-1470 ◽

Cited By ~ 9

Author(s):

Natalia V. Belkova ◽

Oleg A. Filippov ◽

Elena S. Shubina

Keyword(s):

Hydrogen Bonding ◽

Bond Activation ◽

Hydride Transfer ◽

H2 Evolution

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A Bifunctional Copper Catalyst Enables Ester Reduction with H2: Expanding the Reactivity Space of Nucleophilic Copper Hydrides

10.26434/chemrxiv.14730987 ◽

2021 ◽

Author(s):

Birte Zimmermann ◽

Trung Tran Ngoc ◽

Dimitrios-Ioannis Tzaras ◽

Trinadh Kaicharla ◽

Johannes F. Teichert

Keyword(s):

Hydrogen Bonding ◽

Copper Catalyst ◽

Hydride Transfer ◽

Bifunctional Catalyst ◽

Reducing Agents ◽

Reducing Agent ◽

Reduction Step ◽

First Time ◽

The Way

Employing a bifunctional catalyst based on a copper(I)/NHC complex and a guanidine organocatalyst, catalytic ester reductions to alcohols with H2 as terminal reducing agent are facilitated. The approach taken here enables the simul-taneous activation of esters through hydrogen bonding and formation of nucleophilic copper(I) hydrides from H2, resulting in a catalytic hydride transfer to esters. The reduction step is further facilitated by a proton shuttle mediated by the guani-dinium subunit. This bifunctional approach to ester reductions for the first time shifts the reactivity of generally considered “soft” copper(I) hydrides to previously unreactive “hard” ester electrophiles and paves the way for a replacement of stoichi-ometric reducing agents by a catalyst and H2.

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Synergistic promotion by intramolecular hydrogen bonding: a bi-functionally catalyzed cascade reaction for the synthesis of enantiopure chromenopyrrolidines

Organic Chemistry Frontiers ◽

10.1039/c8qo01208c ◽

2019 ◽

Vol 6 (5) ◽

pp. 674-678 ◽

Cited By ~ 3

Author(s):

Jian Cao ◽

Jin-Yu Liu ◽

Yi-Ming Zhang ◽

Zhu-Yin Wang ◽

Peng-Fei Xu

Keyword(s):

Hydrogen Bonding ◽

Intramolecular Hydrogen Bonding ◽

Cascade Reaction ◽

Intramolecular Hydrogen

An effective organocatalytic asymmetric cascade reaction of o-hydroxy aromatic aldimines and β,γ-unsaturated-α-ketoesters was developed.

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A one-pot catalyst/external oxidant/solvent-free cascade approach to pyrimidines via a 1,5-hydride transfer

Green Chemistry ◽

10.1039/c8gc03507e ◽

2019 ◽

Vol 21 (1) ◽

pp. 69-74 ◽

Cited By ~ 17

Author(s):

Mohit L. Deb ◽

Paran J. Borpatra ◽

Pranjal K. Baruah

Keyword(s):

Hydride Transfer ◽

Cascade Reaction ◽

Solvent Free ◽

One Pot ◽

Hydride Shift

A cascade reaction for synthesizing pyrimidines by the functionalization of the C–H bond adjacent to nitrogen through a 1,5-hydride shift is reported.

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A Bifunctional Copper Catalyst Enables Ester Reduction with H2: Expanding the Reactivity Space of Nucleophilic Copper Hydrides

10.26434/chemrxiv.14730987.v1 ◽

2021 ◽

Author(s):

Birte Zimmermann ◽

Trung Tran Ngoc ◽

Dimitrios-Ioannis Tzaras ◽

Trinadh Kaicharla ◽

Johannes F. Teichert

Keyword(s):

Hydrogen Bonding ◽

Copper Catalyst ◽

Hydride Transfer ◽

Bifunctional Catalyst ◽

Reducing Agents ◽

Reducing Agent ◽

Reduction Step ◽

First Time ◽

The Way

Employing a bifunctional catalyst based on a copper(I)/NHC complex and a guanidine organocatalyst, catalytic ester reductions to alcohols with H2 as terminal reducing agent are facilitated. The approach taken here enables the simul-taneous activation of esters through hydrogen bonding and formation of nucleophilic copper(I) hydrides from H2, resulting in a catalytic hydride transfer to esters. The reduction step is further facilitated by a proton shuttle mediated by the guani-dinium subunit. This bifunctional approach to ester reductions for the first time shifts the reactivity of generally considered “soft” copper(I) hydrides to previously unreactive “hard” ester electrophiles and paves the way for a replacement of stoichi-ometric reducing agents by a catalyst and H2.

Download Full-text