Asymmetric construction of atropisomeric biaryls via a redox neutral cross-coupling strategy

Qi, Liangwen; Li, Shaoyu; Xiang, Shao‐Hua; Wang, Jun; Tan, Bin

doi:10.1038/s41929-019-0247-1

Cited by 131 publications

(60 citation statements)

References 48 publications

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“…The packing arrangements and intermolecular interactions of molecules in the solid state measured by single crystal X‐ray studies are often used to explore and design the materials with expected physicochemical properties. This research involve the fields of chemistry, pharmacology, and material science, [ 22 ] and is familiar with devices such as organic light‐emitting transistors, [ 23 ] perovskite solar cells [ 24 ] organic field‐effect transistors, [ 25 ] chiral catalytic synthesis, [ 26 ] and molecular magnet assembly. [ 27 ] The packing modes of molecules are generally divided into H‐ and J‐aggregates, [ 28 ] Figure 1 a shows the H/J‐aggregation states and their energy relationships: [ 29 ] an H‐aggregate is the state of conjugated units whose centers face each other, forming an aggregation state with a slightly higher energy, and manifested as a new aggregation absorption peak in the short wavelength range of UV–visible absorption spectrum; a J‐aggregate is a state of conjugated units centrally parallel but inclined to a certain extent, and with a slightly lower energy, which is manifested as a new aggregation absorption peak in the long wavelength range.…”

Section: Introductionmentioning

confidence: 99%

Crystal Engineering in Organic Photovoltaic Acceptors: A 3D Network Approach

Lai

2020

Advanced Energy Materials

105

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The power conversion efficiency of organic solar cell (OSC) devices has surpassed 18% rapidly. In order to further promote OSC development, it is necessary to understand the packing information at the atomic level to help develop acceptor systems with superior performance. The packing arrangements and intermolecular interactions of these acceptors in the solid state, observed by single crystal X‐ray crystallography, are often used to design materials with expected physicochemical properties. In this review, the chemical structures of acceptors revealed by single crystal X‐ray crystallography are summarized, and the relationship between structural design, packing arrangement, and device properties is discussed. In addition, the concept of “3D network packing” in acceptor systems is proposed, which offers better charge transfer properties in reported chlorinated, fluorinated, brominated, and trifluoromethylated systems, an understanding of 3D network transport also provides guidance in high‐performance materials design. Finally, some current issues related to single crystal studies in OSCs are discussed, with an emphasis on the significance of developing acceptors by understanding and adjusting the aggregation states and intermolecular interactions of materials by single crystal analysis.

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Section: Introductionmentioning

confidence: 99%

Crystal Engineering in Organic Photovoltaic Acceptors: A 3D Network Approach

Lai

2020

Advanced Energy Materials

105

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“…in which an organized hydrogen-bond network activates both the azoarene and the substituted heterocycle. [36] During the following rearomatization ac entral-to-axial chirality conversion is in effect, and the C À Hf unctionalized axially chiral arene is obtained in high atroposelectivity.Adouble enantioselective arene CÀHa mination reaction was conducted with success with (S)-IX,f rom 2,6-diazonaphthalene 69 and carbazoles 70 as the nucleophiles to give the desired 1,5dicarbazole naphthalene derivatives 71 with excellent enantiocontrol (Scheme 19), and only moderate formation of the meso product (dr = 4:1).…”

Section: Methodsmentioning

confidence: 99%

Enantioselective Synthesis of Atropisomers with Multiple Stereogenic Axes

2020

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Atropisomers possessing multiple stereogenic axes are intriguing molecules with huge potential. However, only few approaches for their enantioselective synthesis are available due to the difficulties in assembling various stereogenic axes with high enantiocontrol. Only recently, innovative methods have emerged, opening new possibilities for the synthesis of this original class of atropisomeric compounds. This Minireview describes the development of this field based on a classification of the multi‐axis systems according to the distance between the stereogenic axes and the strategy used to build them.

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“…Using arylazocarboxylates as electrophiles, Tan et al. elegantly achieved the asymmetric arylation of indoles, 2‐naphthols and 2‐naphthylamine (Scheme A) . Furthermore, they also found arylazocarboxylates could act as C−C−N synthons to form axially chiral aniline‐indoles .…”

Section: Methodsmentioning

confidence: 99%

Organocatalytic Enantioselective α‐Amination by Conjugate Addition of 5H‐Thiazol‐4‐ones to Arylazocarboxylates: Access to Chiral N,S‐acetals

et al. 2020

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A chiral phosphoric acid catalyzed stereoselective Michael addition of 5H‐thiazol‐4‐ones to arylazocarboxylates was developed for the construction of optically active N,S‐acetal frameworks. Both 1‐naphthylazocarboxylates and phenylazocarboxylates were compatible to afford a series of 1,4‐adducts in generally high yields and enantioselectivities. Notably, the catalytic protocol enables the formation of N,S‐acetals featuring thiazol‐4‐one skeleton.

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Asymmetric construction of atropisomeric biaryls via a redox neutral cross-coupling strategy

Cited by 131 publications

References 48 publications

Crystal Engineering in Organic Photovoltaic Acceptors: A 3D Network Approach

Crystal Engineering in Organic Photovoltaic Acceptors: A 3D Network Approach

Enantioselective Synthesis of Atropisomers with Multiple Stereogenic Axes

Organocatalytic Enantioselective α‐Amination by Conjugate Addition of 5H‐Thiazol‐4‐ones to Arylazocarboxylates: Access to Chiral N,S‐acetals

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