Reversal of regioselectivity (straight vs. cross ring closure) in the intramolecular [2+2] photocycloaddition of phenanthrene derivatives

Kohmoto, Shigeo; Hisamatsu, Shugo; Mitsuhashi, H.; Takahashi, Masahiro; Masu, Hyuma; Azumaya, Isao; Yamaguchi, Kentaro; Kishikawa, Keiki

doi:10.1039/c000179a

Cited by 11 publications

(3 citation statements)

References 53 publications

(8 reference statements)

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“…258 Tethered approaches were also used to bring about the [2 + 2] photodimerization of more complex β-arylacrylic acids. Along these lines, Noh et al 259 and Kohmoto et al 260 studied the [2 + 2] photodimerization of phenanthrene-9-carboxylic acid derivatives. In the latter study, two acids were linked by a propylamino group via the respective imide 122.…”

Section: Arene-conjugated Alkenesmentioning

confidence: 99%

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

et al. 2016

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The [2 + 2] photocycloaddition is undisputedly the most important and most frequently used photochemical reaction. In this review, it is attempted to cover all recent aspects of [2 + 2] photocycloaddition chemistry with an emphasis on synthetically relevant, regio-, and stereoselective reactions. The review aims to comprehensively discuss relevant work, which was done in the field in the last 20 years (i.e., from 1995 to 2015). Organization of the data follows a subdivision according to mechanism and substrate classes. Cu(I) and PET (photoinduced electron transfer) catalysis are treated separately in sections 2 and 4, whereas the vast majority of photocycloaddition reactions which occur by direct excitation or sensitization are divided within section 3 into individual subsections according to the photochemically excited olefin.

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Section: Arene-conjugated Alkenesmentioning

confidence: 99%

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

et al. 2016

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“…Piling of aromatics can create potential electrically conductive molecular wires . Among the known aromatic folded building blocks, ureas, guanidines, and imides, we employed ureas. For this purpose we developed N , N ′-dimethyl- N , N ′-diphenylureadicarboxylic acid 1 and applied it to the fabrication of triple helices by inclusion of dipyridyl aromatic compounds .…”

Section: Introductionmentioning

confidence: 99%

U-Shaped Aromatic Ureadicarboxylic Acids as Versatile Building Blocks: Construction of Ladder and Zigzag Networks and Channels

Hisamatsu

Masu

Azumaya

et al. 2011

Crystal Growth & Design

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In order to examine versatility of ureadicarboxylic acids as U-shaped building blocks for crystal engineering, their crystal structures and cocrystals with pyridine derivatives were investigated. H-bonding networks created by a sequential linking of H-bonded carboxylic acid dimers resulted in the formation of ladder-type networks in the crystals of N,N 0 -diethyl-N,N 0 -diphenylureadicarboxylic acid (2) and N,N 0 -diallyl-N,N 0 -diphenylureadicarboxylic acid (3). A zigzag type H-bonding network with wedging of water molecules into carboxyÀcarboxy H-bonding was observed for N,N 0 -dibenzyl-N,N 0 -diphenylureadicarboxylic acid (4). Cocrystals of N,N 0 -dimethyl-N,N 0 -diphenylureadicarboxylic acid (1) with 2,5-di(pyridine-4-yl)thiazolo [5,4-d]thiazole (5) and 2 with 4,4 0 -dipyridyl (6) afforded zigzag-type assembled structures. Two types of channel structures were created in the cocrystals of 1 and dipyridylurea (7) by inclusion of water molecules together with either methanol or ethanol. The former afforded a straight-type one-dimensional channel, while the latter afforded a fishnet-type two-dimensional channel.

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“…To the best of our knowledge, this represents the first visible-light-induced CADA cycloaddition where both the donor and acceptor are aromatic units. [43][44][45] Unfortunately, the example with 2-carbonylindole as the excited radical dipole precursor failed to yield the desired cycloadducts (2s), possibly due to the high triplet energy barrier of 2-carbonylindyl compounds. 5 Finally, a diene substrate was attempted as the radical dipole precursor to afford a vinyl cyclobutene as the terminal product (2t), which gave an unidentified complex mixture under the current conditions.…”

Section: A) Coordination-assisted Enantioselective Dearomatization Of...mentioning

confidence: 99%

Enantioselective dearomative ortho-cycloaddition transformation of inactive arenes by cage-confined photocatalysis

Su,

Yang,

et al. 2023

Preprint

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Photoinduced dearomatization of arenes is a powerful strategy in organic synthesis to disrupt the stable aromaticity; however, the asymmetric dearomatization photocatalysis of inactive arenes remains highly challenging and rare. Herein we demonstrate an enzyme-mimicking cage-confined asymmetric photocatalysis method for intramolecular dearomative cycloaddition of electron-deficient β-aryl enones. Owing to the multi-functional synergy of chirality, energy transfer, and host-guest interactions in the confined microenvironments, the self-assembled chiral cage-photoreactor could pre-organize the arenes and activate the β-aryl enones to give stereoselectively fused cyclobutanes through visible-light induced [2+2] ortho-cycloaddition. Notably, the unavoidable transformation to stable [4+2] cycloadducts has been inhibited, producing thermodynamically unfavorable [2+2] cycloadducts with outstanding regio-, diastereo-, and enantioselectivities.

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Reversal of regioselectivity (straight vs. cross ring closure) in the intramolecular [2+2] photocycloaddition of phenanthrene derivatives

Cited by 11 publications

References 53 publications

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

U-Shaped Aromatic Ureadicarboxylic Acids as Versatile Building Blocks: Construction of Ladder and Zigzag Networks and Channels

Enantioselective dearomative ortho-cycloaddition transformation of inactive arenes by cage-confined photocatalysis

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Reversal of regioselectivity (straight vs. cross ring closure) in the intramolecular [2+2] photocycloaddition of phenanthrene derivatives

Cited by 11 publications

References 53 publications

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

U-Shaped Aromatic Ureadicarboxylic Acids as Versatile Building Blocks: Construction of Ladder and Zigzag Networks and Channels

Enantioselective dearomative ortho-cycloaddition transformation of inactive arenes by cage-confined photocatalysis

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Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions