Aryl Chloride-Directed Enantioselective C(sp<sup>2</sup>)-H Borylation Enabled by Iridium Catalysis

Zhao, Hongliang; Zhao, Chao-Yue; Chen, Lili; Xia, Chungu; Hong, Xin; Xu, Senmiao

doi:10.1021/jacs.3c08129

J. Am. Chem. Soc.

2023

DOI: 10.1021/jacs.3c08129

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Aryl Chloride-Directed Enantioselective C(sp²)-H Borylation Enabled by Iridium Catalysis

Hongliang Zhao,

Chao-Yue Zhao,

Lili Chen

et al.

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2024

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Cited by 3 publications

References 79 publications

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Catalytic Enantioselective Primary C–H Borylation for Acyclic All-Carbon Quaternary Stereocenters

Yang,

Chen,

Shi

et al. 2024

J. Am. Chem. Soc.

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Creating a perfect catalyst to operate enzyme-like chiral recognition has been a long-sought aim. A challenging example in this context is constructing acyclic all-carbon quaternary stereogenic centers by transition metal-catalyzed enantioselective C−H activation. We now report highly enantioselective iridium-catalyzed primary C−H borylation of α-all-carbon substituted 2,2-dimethyl amides enabled by a tailor-made chiral bidentate boryl ligand (CBL). The success of the current transformation is attributed to the CBL/iridium catalyst, which has a confined chiral pocket. This protocol provides a diverse array of acyclic all-carbon quaternary stereocenters with excellent enantiocontrol and distinct structural features. Computational study reveals that steric hindrance of CBL could regulate the type of dominant orbital interaction between the catalyst and substrate, which is crucial to conferring high chiral induction.

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Catalytic Enantioselective Primary C–H Borylation for Acyclic All-Carbon Quaternary Stereocenters

Yang,

Chen,

Shi

et al. 2024

J. Am. Chem. Soc.

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Photoinduced Selective B–H Activation of nido-Carboranes

Xu,

Zhang,

et al. 2024

J. Am. Chem. Soc.

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The development of new synthetic methods for B–H bond activation has been an important research area in boron cluster chemistry, which may provide opportunities to broaden the application scope of boron clusters. Herein, we present a new reaction strategy for the direct site-selective B–H functionalization of nido-carboranes initiated by photoinduced cage activation via a noncovalent cage···π interaction. As a result, the nido-carborane cage radical is generated through a single electron transfer from the 3D nido-carborane cage to a 2D photocatalyst upon irradiation with green light. The resulting transient nido-carborane cage radical could be directly probed by an advanced time-resolved EPR technique. In air, the subsequent transformations of the active nido-carborane cage radical have led to efficient and selective B–N, B–S, and B–Se couplings in the presence of N-heterocycles, imines, thioethers, thioamides, and selenium ethers. This protocol also facilitates both the late-stage modification of drugs and the synthesis of nido-carborane-based drug candidates for boron neutron capture therapy (BNCT).

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Chloride-Directed Enantioselective C(sp2)–H Borylation

2024

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Aryl Chloride-Directed Enantioselective C(sp²)-H Borylation Enabled by Iridium Catalysis

Cited by 3 publications

References 79 publications

Catalytic Enantioselective Primary C–H Borylation for Acyclic All-Carbon Quaternary Stereocenters

Catalytic Enantioselective Primary C–H Borylation for Acyclic All-Carbon Quaternary Stereocenters

Photoinduced Selective B–H Activation of nido-Carboranes

Chloride-Directed Enantioselective C(sp2)–H Borylation

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Aryl Chloride-Directed Enantioselective C(sp2)-H Borylation Enabled by Iridium Catalysis

Cited by 3 publications

References 79 publications

Catalytic Enantioselective Primary C–H Borylation for Acyclic All-Carbon Quaternary Stereocenters

Catalytic Enantioselective Primary C–H Borylation for Acyclic All-Carbon Quaternary Stereocenters

Photoinduced Selective B–H Activation of nido-Carboranes

Chloride-Directed Enantioselective C(sp2)–H Borylation

Contact Info

Product

Resources

About

Aryl Chloride-Directed Enantioselective C(sp²)-H Borylation Enabled by Iridium Catalysis