Palladium-catalyzed gaseous CO-free carbonylative C–C bond activation of cyclobutanones

Song, Kun‐Long; Wu, Bin; Gan, Wan‐Er; Yang, Wan‐Chun; Chen, Xiaobing; Cao, Jian; Xu, Li‐Wen

doi:10.1039/d1qo00467k

Cited by 18 publications

(7 citation statements)

References 69 publications

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“…Remarkably, this process would result in a new reductive cross-electrophile coupling to rapidly access synthetically flexible 3-indanone-1-acetic acid scaffolds 2 13 by avoiding the use of hazardous carbon monoxide or its surrogates. 14…”

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confidence: 99%

Merging C–C σ-bond activation of cyclobutanones with CO₂ fixation via Ni-catalysis

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Merging C–C σ-bond activation of cyclobutanones with CO₂ fixation via Ni-catalysis

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“…Although the modular strategy for the synthesis of the above-mentioned atropisomers with superposed axial and point chirality was efficiently realized from chiral starting materials, it would be more useful to obtain novel functional atropisomers through catalytic asymmetric reactions. To develop an efficient stereoselective approach to access optically pure atropisomers, we exploited novel chiral catalytic systems and strategies for the enantioselective synthesis of atropisomers. − We discovered highly efficient chiral TADDOL-derived phosphoramidite ligands for the palladium-catalyzed enantioselective synthesis of a variety of valued chiral compounds with quaternary carbon stereocenters and silicon stereocenters based on the synthetic strategy of desymmetrization. − Our recent findings demonstrated highly efficient chiral TADDOL-derived phosphoramidite ligands for the one-step palladium-catalyzed construction of atropisomeric molecules bearing both axial and central chirality. In this regard, the catalytic asymmetric hydrosilylation of maleimides with hydrosilanes provided silylated carbon stereocenters with high chemo- and enantioselectivity .…”

Section: Catalytic Asymmetric Synthesis Of Atropisomers Bearing Axial...mentioning

confidence: 99%

Atropisomers with Axial and Point Chirality: Synthesis and Applications

et al. 2022

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Conspectus Enantiopure atropisomers have become increasingly important in asymmetric synthesis and catalysis, pharmaceutical science, and material science since the discovery of inherent features of axial chirality originating from rotational restriction. Despite the advances made in this field to date, it remains highly desirable to construct structurally diverse atropisomers with potentially useful functions. We propose superposition to match axial and point chirality as a potentially useful strategy to access structurally complex and diverse building blocks for organic synthesis and pharmaceutical science because merging atropisomeric backbones with one or more extra chiral elements can topologically broaden three-dimensional environments to create complex scaffolds with multiple tunable parameters. Over the past decade, we have successfully implemented a strategic design for the superposition of axial and point chirality to develop a series of enantiopure atropisomers and have utilized the synergistic functions of these molecules to enhance chirality transfer in various catalytic asymmetric transformations. In this Account, we present several novel atropisomers with superposed axial and point chirality developed in our laboratory. In our studies, this superposition strategy was used to design and synthesize both biaryl and non-biaryl atropisomers from commercially available chiral sources. Consequently, these atropisomers were used to demonstrate the importance of the synergetic functions of axial and point chirality in specific enantioselective reactions. For example, aromatic amide-derived atropisomers, simplified as Xing-Phos arrays, were broadly employed in Ag-catalyzed [3 + 2] cycloaddition by a series of reactions of aldiminoesters with activated alkenes and imines, as well as being used as chiral solvating agents for the discrimination of optically active mandelic acid derivatives. Considering the powerful potential of non-biaryl atropisomers for asymmetric catalysis, we also explored the transition-metal-catalyzed enantioselective construction of a novel backbone of non-biaryl atropisomers (Ar–alkene, Ar–N axis) bearing both axial and point chirality for the design and synthesis of chiral ligands and functional molecules. The studies presented herein are expected to stimulate further research efforts on the development of functional atropisomers by superposition of matching axial and point chirality. In addition to tunable electron and stereohindrance effects, the synergy between matching chiral elements of axial/point chirality and functional groups is proven to be a special function that cannot be ignored for promoting reactivity and chirality-transfer efficiency in enantioselective synthesis. Consequently, our novel types of scaffolds with superposed axial and point chirality that are capable of versatile coordination with various metal catalysts in asymmetric catalysis highlight the power of the superposition of matching axial and point chirality for the construction of synthetically useful atropi...

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“…Further, Xu and co-workers also unraveled palladiumcatalyzed carbonylative C−C bond activation of cyclobutanone 185 that proceeds through C−C bond cleavage, ring opening, and amino-or alkoxy-carbonylation (Scheme 70). 74 These tandem C−C bond activation/amino-or alkoxycarbonylation/ carbonylation processes catalyzed by palladium resulted in indanones 193/195 with amide or ester groups. Under gas-free conditions, a variety of indanones containing ester or amide groups are produced by forming two C−C bonds and one C− O or C−N link using the CO surrogate that is phenyl formate and benzene-1,3,5-triyl triformate (TFBen).…”

Section: Vinyl Cyclopropane (Vcp)mentioning

confidence: 99%

Recent Advancement in Palladium-Catalyzed C–C Bond Activation of Strained Ring Systems: Three- and Four-Membered Carbocycles as Prominent C3/C4 Building Blocks

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In recent years, transition metal-catalyzed strong C–C bond activation has significantly attracted the attention of synthetic chemists. This protocol enables simultaneous and direct functionalization of two different M–C bonds. Among different types of C–C bond activation strategies, strain-driven C–C bond activation has resulted in various otherwise difficult transformations. In this context, palladium catalyst has been extensively used and studied due to its robust reactivity and selectivity. Herein we have briefly discussed palladium-catalyzed C–C bond activation of three- and four-membered cycloalkane derivatives.

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Palladium-catalyzed gaseous CO-free carbonylative C–C bond activation of cyclobutanones

Abstract: A palladium-catalyzed carbonylative C–C bond activation reaction of cyclobutanones is reported, and it affords a variety of indanones bearing ester or amide groups using phenyl formate and benzene-1,3,5-triyl triformate as CO surrogates.

Cited by 18 publications

References 69 publications

Merging C–C σ-bond activation of cyclobutanones with CO₂ fixation via Ni-catalysis

Merging C–C σ-bond activation of cyclobutanones with CO₂ fixation via Ni-catalysis

Atropisomers with Axial and Point Chirality: Synthesis and Applications

Recent Advancement in Palladium-Catalyzed C–C Bond Activation of Strained Ring Systems: Three- and Four-Membered Carbocycles as Prominent C3/C4 Building Blocks

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Palladium-catalyzed gaseous CO-free carbonylative C–C bond activation of cyclobutanones

Abstract: A palladium-catalyzed carbonylative C–C bond activation reaction of cyclobutanones is reported, and it affords a variety of indanones bearing ester or amide groups using phenyl formate and benzene-1,3,5-triyl triformate as CO surrogates.

Cited by 18 publications

References 69 publications

Merging C–C σ-bond activation of cyclobutanones with CO2 fixation via Ni-catalysis

Merging C–C σ-bond activation of cyclobutanones with CO2 fixation via Ni-catalysis

Atropisomers with Axial and Point Chirality: Synthesis and Applications

Recent Advancement in Palladium-Catalyzed C–C Bond Activation of Strained Ring Systems: Three- and Four-Membered Carbocycles as Prominent C3/C4 Building Blocks

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Merging C–C σ-bond activation of cyclobutanones with CO₂ fixation via Ni-catalysis

Merging C–C σ-bond activation of cyclobutanones with CO₂ fixation via Ni-catalysis