Nickel-Catalyzed Asymmetric Reductive Cross-Coupling of α-Chloroesters with (Hetero)Aryl Iodides

<a></a><a>An asymmetric reductive cross-coupling of alpha-chloroesters and (hetero)aryl iodides is reported. This nickel-catalyzed reaction proceeds with a chiral BiOX ligand under mild conditions, affording alpha-arylesters in good yields and enantioselectivities. The reaction is tolerant of a variety of functional groups, and the resulting products can be converted to pharmaceutically-relevant chiral building blocks</a>. A multivariate linear regression model was developed to quantitatively relate the influence of the alpha-chloroester substrate and ligand on enantioselectivity

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Nickel-Catalyzed Asymmetric Reductive Cross-Coupling of a-Chloroesters with (Hetero)Aryl Iodides

10.26434/chemrxiv.13474638.v1 ◽

2021 ◽

Author(s):

Travis DeLano ◽

Sara Dibrell ◽

Caitlin Lacker ◽

Adam Pancoast ◽

kelsey poremba ◽

...

Keyword(s):

Linear Regression ◽

Regression Model ◽

Functional Groups ◽

Linear Regression Model ◽

Cross Coupling ◽

Building Blocks ◽

Multivariate Linear Regression Model ◽

Mild Conditions ◽

Aryl Iodides ◽

Reaction Proceeds

<a></a><a>An asymmetric reductive cross-coupling of alpha-chloroesters and (hetero)aryl iodides is reported. This nickel-catalyzed reaction proceeds with a chiral BiOX ligand under mild conditions, affording alpha-arylesters in good yields and enantioselectivities. The reaction is tolerant of a variety of functional groups, and the resulting products can be converted to pharmaceutically-relevant chiral building blocks</a>. A multivariate linear regression model was developed to quantitatively relate the influence of the alpha-chloroester substrate and ligand on enantioselectivity

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Dual Ni/photoredox-catalyzed asymmetric cross-coupling to access chiral benzylic boronic esters

Nature Communications ◽

10.1038/s41467-021-21947-1 ◽

2021 ◽

Vol 12 (1) ◽

Author(s):

Purui Zheng ◽

Pan Zhou ◽

Dong Wang ◽

Wenhao Xu ◽

Hepan Wang ◽

...

Keyword(s):

Visible Light ◽

Ambient Temperature ◽

Functional Group ◽

Cross Coupling ◽

Strong Base ◽

Mild Conditions ◽

Aryl Iodides ◽

Boronic Esters

AbstractThe flourishing Ni/photoredox-catalyzed asymmetric couplings typically rely on redox-neutral reactions. In this work, we report a reductive cross-coupling of aryl iodides and α-chloroboranes under a dual catalytic regime to further enrich the metallaphotoredox chemistry. This approach proceeds under mild conditions (visible light, ambient temperature, no strong base) to access the versatile benzylic boronic esters with good functional group tolerance and excellent enantioselectivities.

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Copper-catalyzed arylation of biguanide derivatives via C–N cross-coupling reactions

Organic & Biomolecular Chemistry ◽

10.1039/c5ob01258a ◽

2015 ◽

Vol 13 (47) ◽

pp. 11432-11437 ◽

Cited By ~ 9

Author(s):

Chen Zhang ◽

Bo Huang ◽

Ai-Qing Bao ◽

Xiao Li ◽

Shunna Guo ◽

...

Keyword(s):

Coupling Reaction ◽

Cross Coupling ◽

Coupling Reactions ◽

Mild Conditions ◽

Cross Coupling Reactions ◽

Aryl Iodides ◽

Cross Coupling Reaction

We developed an efficient copper-catalyzed cross-coupling reaction of biguanide hydrochloride derivatives with both aryl iodides and bromides under mild conditions.

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Iron-catalyzed cross coupling of P–H/C–O bonds: efficient synthesis of α-alkoxyphosphorus compounds

Dalton Transactions ◽

10.1039/c5dt02454d ◽

2016 ◽

Vol 45 (5) ◽

pp. 1877-1880 ◽

Cited By ~ 2

Author(s):

Xue Li ◽

Tieqiao Chen ◽

Yuta Saga ◽

Li-Biao Han

Keyword(s):

Bond Formation ◽

Cross Coupling ◽

Efficient Synthesis ◽

Mild Conditions ◽

Reaction Proceeds ◽

First Time

An efficient P–C bond-formation through iron-catalyzed cross coupling of P–H/C–O bonds is developed for the first time. This reaction proceeds efficiently to produce the corresponding valuable α-alkoxyphosphorus compounds under mild conditions with a wide generality.

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A metal-free radical cascade reaction of phosphine oxides with 2-aryloxy phenylacetylenes to assemble diphosphonyl xanthene derivatives

Organic & Biomolecular Chemistry ◽

10.1039/d1ob01045j ◽

2021 ◽

Author(s):

Tao Fan ◽

Yan Liu ◽

Caina Jiang ◽

Yanli Xu ◽

Yan-Yan Chen

Keyword(s):

Free Radical ◽

Transition Metal ◽

Cascade Reaction ◽

Phosphine Oxides ◽

Metal Free ◽

Mild Conditions ◽

Xanthene Derivatives ◽

Reaction Proceeds ◽

Radical Cascade

A radical cascade reaction of 2-aryloxy phenylacetylene with phosphine oxides promoted by K2S2O8 was developed, provided diphosphonyl xanthenes as products. This reaction proceeds under transition metal-free and mild conditions with...

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