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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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35. Renal Graft Rejection After Allogeneic Peripheral-Blood Stem Cell Transplantation

Author

Barraclough, Katherine A., Robinson, Katherine L., Dowling, John P., Schwarer, Anthony P., and Perry, Gregory J.

Abstract

A 28-year-old woman underwent peripheral-blood stem cell transplantation from her HLA-identical sister for cytogenetic progression of Fanconi anemia. She had received a living-related renal allograft from her father 2 years previously. Nine days after peripheral-blood stem cell transplantation, she developed acute renal failure secondary to acute rejection. Severe microangiopathic hemolysis developed, and cyclosporine therapy was discontinued. Renal biopsy showed humoral rejection and thrombotic microangiopathy. Despite daily plasmapheresis and immunosuppression, she remained dialysis dependent. The renal graft was removed, with rapid resolution of microangiopathic hemolysis. At no stage was there evidence of acute graft-versus-host disease. We speculate that the engrafting third-party hematopoiesis produced acute renal allograft rejection with secondary microangiopathic hemolysis through a graft-versus-graft mechanism.

Published
2006
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37. Thin‐membrane nephropathy — a common cause of glomerular haematuria

Author

Perry, Gregory J., George, Charles R.P., Field, Michael J., Collett, Paul V., Kalowski, Steven, Wyndham, Roger N., Newland, Ronald C., Lin, Betty PC., Kneale, Kennett L., and Lawrence, James R.

Abstract

Thin‐membrane nephropathy recently has been described as a cause of glomerular haematuria. The prognosis of the condition is unclear but it generally is considered to be benign. In a series of 92 patients with glomerular haematuria, thin‐membrane nephropathy was found to be a common cause, occurring in 26 (28%) patients. Sixteen patients were women. The mean age was 42 years. Four patients had a family history of renal disease or haematuria and no patient was deaf. Haematuria had been present from six days to 30 years. Loin pain occurred in 31% of patients. Hypertension was not a feature and mild renal impairment was present in one case only, while a further three cases showed proteinuria at a level of greater than 500 mg of protein per day. Glomerular basement membranes in patients with thin‐membrane nephropathy gave a mean (± standard deviation) width of 319 + 37 nm which was significantly (P< 0.002) less than the control value of 394±61 nm. On the basis of clinical features and serological parameters, thin‐membrane nephropathy could not be separated from other renal causes of haematuria but required careful electronmicroscopic examination of renal biopsy material to establish the diagnosis. Limited follow‐up has confirmed the good prognosis of the condition.

Published
1989
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38. Primary T-cell-rich B-cell lymphoma in the kidney presenting with acute renal failure and a second malignancy

Author

Chin, Kuan C., Perry, Gregory J., Dowling, John P., and Thomson, Napier M.

Abstract

Infiltration of the kidney is commonly found in lymphoma, but acute renal failure arising from bilateral renal infiltration is uncommon. Primary renal lymphoma may occur and is usually of B-cell lineage. It is rare for patients with lymphoma to develop acute renal failure as their initial clinical presentation. Recently, an association between primary renal lymphoma and a second primary malignancy has been reported. We describe the first case of a renal T-cell-rich B-cell lymphoma presenting as acute renal failure, which was associated with a second primary pulmonary malignancy.

Published
1999
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39. 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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40. Primary Sulfonamide Functionalization via Sulfonyl Pyrroles: Seeing the N-Ts Bond in a Different Light.

Author

Ozaki T, Yorimitsu H, and Perry GJP

Subjects
Pyrroles, Sulfonamides
Abstract

Despite common occurrence in molecules of value, methods for transforming sulfonamides are distinctly lacking. Here we introduce easy-to-access sulfonyl pyrroles as synthetic linchpins for sulfonamide functionalization. The versatility of the sulfonyl pyrrole unit is shown by generating a variety of products through chemical, electrochemical and photochemical pathways. Preliminary results on the direct functionalization of primary sulfonamides are also provided, which may lead to new modes of activation., (© 2021 Wiley-VCH GmbH.)

Published
2021
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41. Copper-Catalyzed Borylative Couplings with C-N Electrophiles.

Author

Talbot FJT, Dherbassy Q, Manna S, Shi C, Zhang S, Howell GP, Perry GJP, and Procter DJ

Abstract

Copper-catalyzed borylative multicomponent reactions (MCRs) involving olefins and C-N electrophiles are a powerful tool to rapidly build up molecular complexity. The products from these reactions contain multiple functionalities, such as amino, cyano and boronate groups, that are ubiquitous in medicinal and process chemistry programs. Copper-catalyzed MCRs are particularly attractive because they use a relatively abundant and non-toxic catalyst to selectively deliver high-value products from simple feedstocks such as olefins. In this Minireview, we explore this rapidly emerging field and survey the borylative union of allenes, dienes, styrenes and other olefins, with imines, nitriles and related C-N electrophiles., (© 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.)

Published
2020
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42. Trifluoromethyl Sulfoxides: Reagents for Metal-Free C-H Trifluoromethylthiolation.

Author

Wang D, Carlton CG, Tayu M, McDouall JJW, Perry GJP, and Procter DJ

Abstract

Trifluoromethyl sulfoxides are a new class of trifluoromethylthiolating reagent. The sulfoxides engage in metal-free C-H trifluoromethylthiolation with a range of (hetero)arenes. The method is also applicable to the functionalization of important compound classes, such as ligand derivatives and polyaromatics, and in the late-stage trifluoromethylthiolation of medicines and agrochemicals. The isolation and characterization of a sulfonium salt intermediate supports an interrupted Pummerer reaction mechanism., (© 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.)

Published
2020
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43. Enantio- and Diastereoselective Synthesis of Homopropargyl Amines by Copper-Catalyzed Coupling of Imines, 1,3-Enynes, and Diborons.

Author

Manna S, Dherbassy Q, Perry GJP, and Procter DJ

Abstract

An efficient, enantio- and diastereoselective, copper-catalyzed coupling of imines, 1,3-enynes, and diborons is reported. The process shows broad substrate scope and delivers complex, chiral homopropargyl amines; useful building blocks on the way to biologically-relevant compounds. In particular, functionalized homopropargyl amines bearing up to three contiguous stereocenters can be prepared in a single step., (© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)

Published
2020
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