The Gold(I)-Catalyzed Cycloisomerization of 1,6-Enynes to 1,4-Dienes

Lee, Jun Young; Kim, Soo Min; Kim, Sun Young; Chung, Young Keun

doi:10.1055/s-2006-949629

Cited by 8 publications

(1 citation statement)

References 2 publications

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“…There are even more excellent strategies of regulating aggregate state to enhance the CPL by self‐assembly, liquid crystal, metal‐organic framework, polymer matrix, crystallization, supramolecular encapsulation, and chiral cage [59–63] . These results further confirm that CPL enhancement can be achieved by increasing rigidity and enhancing interactions [64] . However, a systematic and comprehensive demonstration of the structure‐property relationship between the restriction of molecular motions and the enhancement of CPL performance is still lacking.…”

Section: Introductionmentioning

confidence: 86%

Boosting Circularly Polarized Luminescence from Alkyl‐Locked Axial Chirality Scaffold by Restriction of Molecular Motions

Huang,

Zhu,

Zhou

et al. 2024

Chemistry A European J

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Boosting the circularly polarized luminescence of small organic molecules has been a stubborn challenge because of weak structure rigidity and dynamic molecular motions. To investigate and eliminate these factors, here, we carried out the structure‐property relationship studies on a newly‐developed axial chiral scaffold of bidibenzo[b,d]furan. The molecular rigidity was finely tuned by gradually reducing the alkyl‐chain length. The environmental factors were considered in solution, crystal, and polymer matrix at different temperatures. As a result, a significant amplification of the dissymmetry factor glum from 10‐4 to 10‐1 was achieved, corresponding to the situation from (R)‐4C in solution to (R)‐1C in polymer film at room temperature. A synergistic strategy of increasing the intramolecular rigidity and enhancing the intermolecular interaction to restrict the molecular motions was thus proposed to improve circularly polarized luminescence. The though‐out demonstrated relationship will be of great importance for the development of high‐performance small organic chiroptical systems in the future.

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Section: Introductionmentioning

confidence: 86%

Boosting Circularly Polarized Luminescence from Alkyl‐Locked Axial Chirality Scaffold by Restriction of Molecular Motions

Huang,

Zhu,

Zhou

et al. 2024

Chemistry A European J

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Cycloisomerization of 1,n-Enynes Via Carbophilic Activation

Toullec

Michelet

2011

Topics in Current Chemistry

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Metal-catalyzed cycloisomerization of 1,n-enynes has appeared as a highly attractive methodology for the synthesis of original carbo- and heterocycles. This chapter intends to propose an overview of the recent and seminal advances in 1,n-enynes cycloisomerization reactions in the presence of carbophilic transition metals. The recent mechanistic insights, the enantioselective versions, and the applications in total synthesis are highlighted.

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Synthesis of Pyrrole and Carbazole Alkaloids

Бауер

Knölker

2011

Topics in Current Chemistry

203

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An overview of recent transition metal-catalyzed syntheses of pyrroles and carbazoles is presented. The focus is on methods which have been applied to the preparation of biologically active naturally occurring pyrrole and carbazole alkaloids. For pyrroles, special attention is paid to silver(I)-catalyzed cyclization reactions. For carbazoles, iron(0)-mediated and palladium(0/II)-catalyzed cyclization reactions are highlighted and their broad range of applications is discussed.

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The Gold(I)-Catalyzed Cycloisomerization of 1,6-Enynes to 1,4-Dienes

Abstract: Cycloisomerization of 1,6-enynes to 1,4-dienes proceeded smoothly in the presence of a gold(I) catalyst under mild reaction conditions, and cyclized 1,4-dienes were isolated in good yields. The catalytic system can tolerate the oxygen and nitrogen tether in the substrate.

Cited by 8 publications

References 2 publications

Boosting Circularly Polarized Luminescence from Alkyl‐Locked Axial Chirality Scaffold by Restriction of Molecular Motions

Boosting Circularly Polarized Luminescence from Alkyl‐Locked Axial Chirality Scaffold by Restriction of Molecular Motions

Cycloisomerization of 1,n-Enynes Via Carbophilic Activation

Synthesis of Pyrrole and Carbazole Alkaloids

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