Rhodium-catalyzed addition reactions of benzylic C–H bonds to cyclic N-sulfonyl ketimines via π-coordination

Li, Yuntong; Shi, Hang

doi:10.1016/j.cclet.2023.108650

“…In 2022, the Shi group demonstrated that Rh(III) catalysts can significantly enhance benzylic C–H bond deprotonation through π-coordination to the aromatic ring, leading to efficient formation of benzylic carbanions . This enabled the stereoselective deuteration of benzylic C–H bonds and benzylic addition reactions.…”

Section: π-Coordination Activation Strategymentioning

confidence: 99%

Transition-Metal-Catalyzed Dehydrogenative (3 + 2) Annulation of Aromatic Compounds: Synthesis of Indenes and Indanes via Dual Functionalization of Benzylic and ortho C–H Bonds

Wu,

Shi

2023

J. Org. Chem.

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Intermolecular (3 + 2) annulation emerges as a potent approach for constructing 5-membered carbocycles through the fusion of two distinct components. This synopsis encapsulates recent strides in the realm of transition-metal-catalyzed dehydrogenative (3 + 2) annulation of aromatic hydrocarbons, achieved through the dual functionalization of benzylic and ortho C−H bonds. Encompassing three pivotal strategies, namely, (i) C−H bond activation, (ii) benzylic oxidation, and (iii) π-coordination activation, this review offers an overview of the field's recent developments.

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Recent Advances in Dearomative Partial Reduction of Benzenoid Arenes

Liu,

Ma

2024

Angewandte Chemie

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Dearomative partial reduction is an extraordinary approach for transforming benzenoid arenes and has been well‐known for many decades, as demonstrated by the dihydrogenation in Birch reduction and the hydroarylation in Crich addition. Despite its significant importance in synthesis, this field has experienced slow progress over the last half‐century. However, a revival has been observed with the recent introduction of electrochemical and photochemical methods. In this Minireview, we summarize the recent advancements in dearomative partial reduction of benzenoid arenes, including dihydrogenation, hydroalkylation, arylation, alkenylation, amination, borylation and others. Further, the intriguing utilization of dearomative partial reduction in the synthesis of natural products is also highlighted. It is anticipated that this Minireview will stimulate further progress in arene dearomative transformations.

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Recent Advances in Dearomative Partial Reduction of Benzenoid Arenes

Liu,

Ma

2024

Angew Chem Int Ed

4

0

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Dearomative partial reduction is an extraordinary approach for transforming benzenoid arenes and has been well‐known for many decades, as demonstrated by the dihydrogenation in Birch reduction and the hydroarylation in Crich addition. Despite its significant importance in synthesis, this field has experienced slow progress over the last half‐century. However, a revival has been observed with the recent introduction of electrochemical and photochemical methods. In this Minireview, we summarize the recent advancements in dearomative partial reduction of benzenoid arenes, including dihydrogenation, hydroalkylation, arylation, alkenylation, amination, borylation and others. Further, the intriguing utilization of dearomative partial reduction in the synthesis of natural products is also highlighted. It is anticipated that this Minireview will stimulate further progress in arene dearomative transformations.

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Rhodium-catalyzed addition reactions of benzylic C–H bonds to cyclic N-sulfonyl ketimines via π-coordination

Cited by 5 publications

References 66 publications

Transition-Metal-Catalyzed Dehydrogenative (3 + 2) Annulation of Aromatic Compounds: Synthesis of Indenes and Indanes via Dual Functionalization of Benzylic and ortho C–H Bonds

Transition-Metal-Catalyzed Dehydrogenative (3 + 2) Annulation of Aromatic Compounds: Synthesis of Indenes and Indanes via Dual Functionalization of Benzylic and ortho C–H Bonds

Recent Advances in Dearomative Partial Reduction of Benzenoid Arenes

Recent Advances in Dearomative Partial Reduction of Benzenoid Arenes

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