Nickel-Catalyzed Asymmetric Ring Opening of Oxabenzonorbornadienes with Arylboronic Acids

Zeng, Zhongyi; Yang, Dingqiao; Long, Yuhua; Pan, Xuejing; Huang, Guobao; Zuo, Xiongjun; Zhou, Wen

doi:10.1021/jo500821m

Cited by 33 publications

(13 citation statements)

References 70 publications

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“…Their asymmetric ring opening by arylboronic acids has attracted considerable attention as it offers a straightforward access to chiral aryltetralins, which are common substructures in bioactive natural products (Scheme 15). After seminal work by Lautens and co‐workers using rhodium in combination with ferrocenylphosphine catalysts, [56] other metal‐catalyzed procedures for the asymmetric arylative ring opening of oxabenzonorbornadienes with arylboronic acids emerged in the more recent literature [57,58] …”

Section: Boronic Acids and Derivativesmentioning

confidence: 99%

Boron Reagents and Catalysts for the Functionalization of Strained Heterocycles

Pineschi

2021

Adv Synth Catal

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The particular nature of boron compounds allows an ample modularity of their properties ranging from Lewis acids, C‐nucleophiles, B‐nucleophiles, or even conjunctive reagents for new synthetic manipulations. Moreover, the increasing demand for functionalized boron derivatives for pharmaceutical or material science applications requires the development of new synthetic methods for boron introduction in organic compounds. This review summarizes the possible combinations of boron derivatives with a variety of strained heterocycles reported in the most recent literature.

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Section: Boronic Acids and Derivativesmentioning

confidence: 99%

Boron Reagents and Catalysts for the Functionalization of Strained Heterocycles

Pineschi

2021

Adv Synth Catal

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“…When substituents existed on OBD, electronic properties were more important, with electron-withdrawing groups being more reactive. With few exceptions, these reactions gave very high yields and enantioselectivities [ 52 ].…”

Section: Transition Metal Catalyzed Reactions Of Obdmentioning

confidence: 99%

“…46 Transmetalates with the arylboronic acid, previously activated by a base, to form the (alkenyl)-(π-allyl)-nickel (II) intermediate 47 . The final product 45 is formed by reductive elimination and protonolysis, and the active Ni (0) catalyst is regenerated (Scheme 22 ) [ 52 ].…”

Section: Transition Metal Catalyzed Reactions Of Obdmentioning

confidence: 99%

Recent Advances in Transition Metal-Catalyzed Reactions of Oxabenzonorbornadiene

Boutin

Koh

Tam

2019

COS

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Background: Oxabenzonorbornadiene (OBD) is a useful synthetic intermediate capable of undergoing multiple types of transformations due to three key structural features: a free alkene, a bridged oxygen atom, and a highly strained ring system. Most notably, ring-opening reactions of OBD using transition metal catalysts and nucleophiles produce multiple stereocenters in a single step. The resulting dihydronaphthalene framework is found in many natural products, which have been shown to be biologically active. Objective: This review will provide an overview of transition metal-catalyzed reactions from the past couple of years including cobalt, copper, iridium, nickel, palladium and rhodium- catalyzed reactions. In addition, the recent derivatization of OBD to cyclopropanated oxabenzonorbornadiene and its reactivity will be discussed. Conclusion: It can be seen from the review, that the work done on this topic has employed the use of many different transition metal catalysts, with many different nucleophiles, to perform various transformations on the OBD molecule. Additionally, depending on the catalyst and ligand used, the stereo and regioselectivity of the product can be controlled, with proposed mechanisms to support the understanding of such reactions. The use of palladium has also generated a cyclopropanated OBD, with reactivity similar to that of OBD. An additional reactive site exists at the distal cyclopropane carbon, giving rise to three types of ring-opened products.

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“…Various aryl donators, such as aryl halides, organometallic reagents, and arylboronic acids, have been applied in this type of reaction. The study referring to the reactions of oxabenzonorbornadiene with aryl halides is relatively rare because of the low activity of aryl halides.…”

Section: Introductionmentioning

confidence: 99%

Palladium-Catalyzed syn-Stereocontrolled Ring-Opening of Oxabicyclic Alkenes with Sodium Arylsulfinates

Yang

Guo

et al. 2016

J. Org. Chem.

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Palladium-catalyzed syn-stereocontrolled ring-opening reactions of oxabenzonorbornadienes with a wide range of sodium arylsulfinates were investigated, affording the desired products in good to excellent yields under an air atmosphere. This protocol provides a low-cost new viable and convenient method toward the synthesis of cis-2-aryl-1,2-dihydronaphthalen-1-ol with good functional group tolerance. In addition, the cis configuration of 3da was established by X-ray diffraction analysis, and a plausible mechanism for the ring-opening reaction was proposed.

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Nickel-Catalyzed Asymmetric Ring Opening of Oxabenzonorbornadienes with Arylboronic Acids

Cited by 33 publications

References 70 publications

Boron Reagents and Catalysts for the Functionalization of Strained Heterocycles

Boron Reagents and Catalysts for the Functionalization of Strained Heterocycles

Recent Advances in Transition Metal-Catalyzed Reactions of Oxabenzonorbornadiene

Palladium-Catalyzed syn-Stereocontrolled Ring-Opening of Oxabicyclic Alkenes with Sodium Arylsulfinates

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