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Your search keyword '"Perry, Gregory J. P."' showing total 34 results
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34 results on '"Perry, Gregory J. P."'

6. Sulfonium-aided coupling of aromatic rings via sigmatropic rearrangement

Author

00372566, YORIMITSU, Hideki, PERRY, Gregory J. P., 00372566, YORIMITSU, Hideki, and PERRY, Gregory J. P.

Abstract

Biaryl synthesis continues to occupy a central role in chemical synthesis. From blockbuster drug molecules to organic electronics, biaryls present numerous possibilities and new applications continue to emerge. Transition-metal-catalyzed coupling reactions represent the gold standard for biaryl synthesis and the mechanistic steps, such as reductive elimination, are well established. Developing routes that exploit alternative mechanistic scenarios could give unprecedented biaryl structures and expand the portfolio of biaryl applications. We have developed metal-free C–H/C–H couplings of aryl sulfoxides with phenols to afford 2-hydroxy-2′-sulfanylbiaryls. This cascade strategy consists of an interrupted Pummerer reaction and [3, 3] sigmatropic rearrangement. Our method enables the synthesis of intriguing aromatic molecules, including oligoarenes, enantioenriched dihetero[8]helicenes, and polyfluorobiaryls. From our successes in aryl sulfoxide/phenol couplings and a deeper understanding of sigmatropic rearrangements for biaryl synthesis, we have established related methods, such as aryl sulfoxide/aniline and aryl iodane/phenol couplings. Overall, our fundamental interests in underexplored reaction mechanisms have led to various methods for accessing important biaryl architectures.

Published
2022

9. Modular synthesis of unsymmetrical [1]benzothieno[3,2-b][1]benzothiophene molecular semiconductors for organic transistors

Author

Tayu, Masanori, primary, Rahmanudin, Aiman, additional, Perry, Gregory J. P., additional, Khan, Raja U., additional, Tate, Daniel J., additional, Marcial-Hernandez, Raymundo, additional, Shen, Yuan, additional, Dierking, Ingo, additional, Janpatompong, Yurachat, additional, Aphichatpanichakul, Suphaluk, additional, Zamhuri, Adibah, additional, Victoria-Yrezabal, Inigo, additional, Turner, Michael L., additional, and Procter, David J., additional

Published
2022
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16. Transition-metal-free decarboxylative bromination of aromatic carboxylic acids† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c8sc01016a

Author

Quibell, Jacob M., Perry, Gregory J. P., Cannas, Diego M., and Larrosa, Igor

Subjects
Chemistry
Abstract

Aromatic acids are converted into aryl bromides simply and efficiently via decarboxylation providing new depth and insight into Hunsdiecker-type reactivity., Methods for the conversion of aliphatic acids to alkyl halides have progressed significantly over the past century, however, the analogous decarboxylative bromination of aromatic acids has remained a longstanding challenge. The development of efficient methods for the synthesis of aryl bromides is of great importance as they are versatile reagents in synthesis and are present in many functional molecules. Herein we report a transition metal-free decarboxylative bromination of aromatic acids. The reaction is applicable to many electron-rich aromatic and heteroaromatic acids which have previously proved poor substrates for Hunsdiecker-type reactions. In addition, our preliminary mechanistic study suggests that radical intermediates are not involved in this reaction, which is in contrast to classical Hunsdiecker-type reactivity. Overall, the process demonstrates a useful method for producing valuable reagents from inexpensive and abundant starting materials.

Published
2018

18. Metal-free synthesis of benzothiophenes via 2-fold C-H functionalization: direct access to materials-oriented heteroaromatics

Author

Yan, Jiajie, Pulis, Alexander P, Perry, Gregory J. P., and Procter, David John

Subjects
pummerer, sulfur, benzothiophene, annulation
Abstract

Due to their ubiquity in nature and frequent use in organic electronic materials, benzothiophenes are highly sought after. Here we set out an unprecedented procedure for the formation of benzothiophenes via the dual vicinal C–H functionalization of arenes that does not require metal catalysis. This one‐pot annulation proceeds through an interrupted Pummerer reaction/[3,3]‐sigmatropic rearrangement/cyclization sequence to deliver various benzothiophene products. The procedure is particularly effective for the rapid synthesis of benzothiophenes from non‐prefunctionalized polyaromatic hydrocarbons (PAHs).

Published
2019
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21. Copper-catalyzed functionalization of enynes

Author

Dherbassy, Quentin, primary, Manna, Srimanta, additional, Talbot, Fabien J. T., additional, Prasitwatcharakorn, Watcharapon, additional, Perry, Gregory J. P., additional, and Procter, David J., additional

Published
2020
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34. Modular synthesis of unsymmetrical [1]benzothieno[3,2- b ][1]benzothiophene molecular semiconductors for organic transistors.

Author

Tayu M, Rahmanudin A, Perry GJP, Khan RU, Tate DJ, Marcial-Hernandez R, Shen Y, Dierking I, Janpatompong Y, Aphichatpanichakul S, Zamhuri A, Victoria-Yrezabal I, Turner ML, and Procter DJ

Abstract

A modular approach to underexplored, unsymmetrical [1]benzothieno[3,2- b ][1]benzothiophene (BTBT) scaffolds delivers a library of BTBT materials from readily available coupling partners by combining a transition-metal free Pummerer CH-CH-type cross-coupling and a Newman-Kwart reaction. This effective approach to unsymmetrical BTBT materials has allowed their properties to be studied. In particular, tuning the functional groups on the BTBT scaffold allows the solid-state assembly and molecular orbital energy levels to be modulated. Investigation of the charge transport properties of BTBT-containing small-molecule:polymer blends revealed the importance of molecular ordering during phase segregation and matching the highest occupied molecular orbital energy level with that of the semiconducting polymer binder, polyindacenodithiophene-benzothiadiazole (PIDTBT). The hole mobilities extracted from transistors fabricated using blends of PIDTBT with phenyl or methoxy functionalized unsymmetrical BTBTs were double those measured for devices fabricated using pristine PIDTBT. This study underscores the value of the synthetic methodology in providing a platform from which to study structure-property relationships in an underrepresented family of unsymmetrical BTBT molecular semiconductors., Competing Interests: There are no conflicts to declare., (This journal is © The Royal Society of Chemistry.)

Published
2021
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