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Search for "boronic acid" in Full Text gives 144 result(s) in Beilstein Journal of Organic Chemistry.

Synthesis of benzo[f]quinazoline-1,3(2H,4H)-diones

  • Ruben Manuel Figueira de Abreu,
  • Peter Ehlers and
  • Peter Langer

Beilstein J. Org. Chem. 2024, 20, 2708–2719, doi:10.3762/bjoc.20.228

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  • (PPh3)4 (10 mol %), NaOH (3 equiv), 1,4-dioxane/water 5:1, 100 °C, 1 h; iv) p-TsOH (20 equiv), toluene, 100 °C, 4 h. Synthesis and isolated yields of 1,3-dimethyl-5-aryl-6-[2-(aryl)ethynyl]uracils 4a–i. Reaction conditions: 3 (1 equiv), boronic acid (1.2 equiv), Pd(PPh3)4 (5 mol %), NaOH (3 equiv), 1,4
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Published 28 Oct 2024

Synthesis of fluoroalkenes and fluoroenynes via cross-coupling reactions using novel multihalogenated vinyl ethers

  • Yukiko Karuo,
  • Keita Hirata,
  • Atsushi Tarui,
  • Kazuyuki Sato,
  • Kentaro Kawai and
  • Masaaki Omote

Beilstein J. Org. Chem. 2024, 20, 2691–2703, doi:10.3762/bjoc.20.226

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  • and 11). We predicted that the product yield would decrease because 2k is labile in column chromatography. Utilizing a boronic acid bearing an n-butyl group as a primary alkyl group (4m), the cross-coupling did not proceed due to β-elimination (Table 3, entry 12). In contrast, the reaction with
  • mol %), cesium carbonate (1.5 equiv), palladium bis(trifluoroacetate) (5 mol %) in THF (2.0 mL) was added the respective boronic acid derivative 4 (2.0 equiv). The reaction solution was refluxed for 3.5 h. The reaction mixture was quenched by the addition of water (40 mL) at 0 °C and extracted with
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Published 24 Oct 2024

Multicomponent syntheses of pyrazoles via (3 + 2)-cyclocondensation and (3 + 2)-cycloaddition key steps

  • Ignaz Betcke,
  • Alissa C. Götzinger,
  • Maryna M. Kornet and
  • Thomas J. J. Müller

Beilstein J. Org. Chem. 2024, 20, 2024–2077, doi:10.3762/bjoc.20.178

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  • arylhydrazines 116 are used as starting materials. The p-bromophenylpyrazoles presented in situ can be reacted with boronic acids or boronic acid esters in a sequentially Pd-catalyzed coupling towards biaryl-substituted pyrazoles 113, 115, and 117 (Scheme 41) [138]. Furthermore, a pseudo-five-component reaction
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Published 16 Aug 2024

The Groebke–Blackburn–Bienaymé reaction in its maturity: innovation and improvements since its 21st birthday (2019–2023)

  • Cristina Martini,
  • Muhammad Idham Darussalam Mardjan and
  • Andrea Basso

Beilstein J. Org. Chem. 2024, 20, 1839–1879, doi:10.3762/bjoc.20.162

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  • temperature and then, upon addition of the boronic acid, heating at 60 °C (Scheme 9). Similar efficiencies were observed with a wide range of boronic acids (10 examples, 49–87% yield). The biohybrid was suitable also for gram-scale synthesis and for storage at room temperature under inert atmosphere, showing
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Published 01 Aug 2024

Syntheses and medicinal chemistry of spiro heterocyclic steroids

  • Laura L. Romero-Hernández,
  • Ana Isabel Ahuja-Casarín,
  • Penélope Merino-Montiel,
  • Sara Montiel-Smith,
  • José Luis Vega-Báez and
  • Jesús Sandoval-Ramírez

Beilstein J. Org. Chem. 2024, 20, 1713–1745, doi:10.3762/bjoc.20.152

Graphical Abstract
  • out, resulting in the corresponding N-tosylhydrazones 51a–c. Afterwards, the compounds were subjected to microwave irradiation in the presence of (3-azidopropyl)boronic acid and potassium or cesium carbonate, yielding 3-spiropyrrolidines 52a–c in high overall yields as 1:1 mixture of diastereomers
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Published 24 Jul 2024

Competing electrophilic substitution and oxidative polymerization of arylamines with selenium dioxide

  • Vishnu Selladurai and
  • Selvakumar Karuthapandi

Beilstein J. Org. Chem. 2024, 20, 1221–1235, doi:10.3762/bjoc.20.105

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  • ]. This reaction comprises four main steps: (i) iodide-mediated aryl transfer from boronic acid to selenium dioxide, (ii) reduction of arylseleninic acid to diaryl diselenide, (iii) oxidation of diaryl diselenide to aryl selenenyl iodide with iodine, and (iv) electrophilic substitution of aniline
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Published 27 May 2024

Synthesis and properties of 6-alkynyl-5-aryluracils

  • Ruben Manuel Figueira de Abreu,
  • Till Brockmann,
  • Alexander Villinger,
  • Peter Ehlers and
  • Peter Langer

Beilstein J. Org. Chem. 2024, 20, 898–911, doi:10.3762/bjoc.20.80

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  • low yield of the first approach. Replacing the catalyst and increasing the temperature or the amount of boronic acid proved to be unsuccessful. With entry 6 (Table 1) it was shown that similar yields could be obtained by removing the ligand and using higher amounts of catalyst. Therefore, no
  • synthesis of 5a–t. A mixture of 3a (303 µmol; 109 mg), Pd(PPh3)4 (10 mol %; 369 µmol; 5 mg), NaOH (3.0 equiv; 933 µmol; 37 mg) and the corresponding boronic acid (4-tolylboronic acid, 1.2 equiv; 369 µmol; 5 mg) was dissolved in a mixture of 1,4-dioxane and water 5:1. The reaction mixture was heated to 100
  • . Synthesis of 1,3-dimethyl-5-aryl-6-[2-(aryl)ethynyl]uracils 5a–t. Reaction conditions: 3 (1 equiv), boronic acid (1.2 equiv), Pd(PPh3)4 (5 mol %), NaOH (3 equiv), dioxane/water 5:1, 100 °C, 1 h. aYields of isolated products. Optimization of the reaction conditions for the synthesis of 5a. Photophysical data
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Published 22 Apr 2024

(Bio)isosteres of ortho- and meta-substituted benzenes

  • H. Erik Diepers and
  • Johannes C. L. Walker

Beilstein J. Org. Chem. 2024, 20, 859–890, doi:10.3762/bjoc.20.78

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  • obtain the 1,3-cuneane selectively. The hydroxymethyl group (185a, 185b, 185f), a boronic acid pinacol ester (185c), a phthalimide-protected aminomethyl group (185d) and an oxazole (185e) were, among others, successful as electron-donating groups yielding 1,3-cuneanes. Iwabuchi and co-workers also found
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Published 19 Apr 2024

Ortho-ester-substituted diaryliodonium salts enabled regioselective arylocyclization of naphthols toward 3,4-benzocoumarins

  • Ke Jiang,
  • Cheng Pan,
  • Limin Wang,
  • Hao-Yang Wang and
  • Jianwei Han

Beilstein J. Org. Chem. 2024, 20, 841–851, doi:10.3762/bjoc.20.76

Graphical Abstract
  • acid, trifluoroborate moiety, trifluoromethanesulfonate, aryl sulfonamides, and heterocycles, have been incorporated into the ortho-position of diaryliodonium structures [16][17][18][19][20][21]. Ortho-trimethylsilyl or boronic acid-substituted diaryliodonium salts can serve as aryne precursors. Ortho
  • , expanding the benzocoumarin family (Scheme 1b) [14]. Recently, ortho-functionalized diaryliodonium salts, due to their coordinating and electrophilic effects, have exhibited unique reactivity and chemoselectivity [15]. As such, a wide range of functional groups including the trimethylsilyl group, boronic
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Published 18 Apr 2024

Switchable molecular tweezers: design and applications

  • Pablo Msellem,
  • Maksym Dekthiarenko,
  • Nihal Hadj Seyd and
  • Guillaume Vives

Beilstein J. Org. Chem. 2024, 20, 504–539, doi:10.3762/bjoc.20.45

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Published 01 Mar 2024

Mono or double Pd-catalyzed C–H bond functionalization for the annulative π-extension of 1,8-dibromonaphthalene: a one pot access to fluoranthene derivatives

  • Nahed Ketata,
  • Linhao Liu,
  • Ridha Ben Salem and
  • Henri Doucet

Beilstein J. Org. Chem. 2024, 20, 427–435, doi:10.3762/bjoc.20.37

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  • adjacent or between the two fluorine atoms in these arenes. The synthesis of these two fluoranthene derivatives by Suzuki coupling followed by intramolecular C–H activation was therefore investigated. From (3,4-difluorophenyl)boronic acid and (3,5-difluorophenyl)boronic acid, target products 25 and 26 were
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Published 23 Feb 2024

Synthesis of π-conjugated polycyclic compounds by late-stage extrusion of chalcogen fragments

  • Aissam Okba,
  • Pablo Simón Marqués,
  • Kyohei Matsuo,
  • Naoki Aratani,
  • Hiroko Yamada,
  • Gwénaël Rapenne and
  • Claire Kammerer

Beilstein J. Org. Chem. 2024, 20, 287–305, doi:10.3762/bjoc.20.30

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  • corresponding boronic acid 9 and a Suzuki–Miyaura cross-coupling between 8 and 9 gave rise to dimer 10, followed by the oxidation of both acenaphthene units into 1,8-naphthalic anhydrides. Installation of the thiepine ring was achieved by a double nucleophilic aromatic substitution induced by sodium sulfide
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Published 15 Feb 2024

Metal-catalyzed coupling/carbonylative cyclizations for accessing dibenzodiazepinones: an expedient route to clozapine and other drugs

  • Amina Moutayakine and
  • Anthony J. Burke

Beilstein J. Org. Chem. 2024, 20, 193–204, doi:10.3762/bjoc.20.19

Graphical Abstract
  • coupling: o-Phenylenediamine (1a, 0.05 g, 1 equiv, 0.46 mmol) was added to a round-bottomed flask and dissolved in dry dioxane (5 mL). Next, 2-bromophenyl)boronic acid (7, 0.092 g, 1 equiv,0.46 mmol) was added, followed by the addition of Et3N (0.07 mL, 0.055 mmol), CuI (0.018 g, 0.092 mmol, 20 mol %), and
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Published 31 Jan 2024

Synthesis of N-acyl carbazoles, phenoxazines and acridines from cyclic diaryliodonium salts

  • Nils Clamor,
  • Mattis Damrath,
  • Thomas J. Kuczmera,
  • Daniel Duvinage and
  • Boris J. Nachtsheim

Beilstein J. Org. Chem. 2024, 20, 12–16, doi:10.3762/bjoc.20.2

Graphical Abstract
  • % yields. para-Amino- and boronic acid-substituted benzamides did not react. While meta-bromo-substituted benzamide gave 2j in 84% yield, ortho-bromination resulted in a diminished yield of 2k (55%). We obtained 3,5-disubstituted N-acyl carbazoles 2l and 2m in 91% and 88% yields. The same disubstitution
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Published 04 Jan 2024

Consecutive four-component synthesis of trisubstituted 3-iodoindoles by an alkynylation–cyclization–iodination–alkylation sequence

  • Nadia Ledermann,
  • Alae-Eddine Moubsit and
  • Thomas J. J. Müller

Beilstein J. Org. Chem. 2023, 19, 1379–1385, doi:10.3762/bjoc.19.99

Graphical Abstract
  • , 63.81; H, 3.74; N, 2.96. Synthesis of 1,2,3-trisubstituted indole 8b (typical procedure) 3-Iodoindole 5a (167 mg, 0.50 mmol), (p-tolyl)boronic acid (7b, 204 mg, 1.50 mmol), Pd(PPh3)4 (28.9 mg, 25.0 μmol), and cesium carbonate (652 mg, 2.00 mmol) were placed in an oven-dried Schlenk tube with magnetic
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Published 14 Sep 2023

Construction of hexabenzocoronene-based chiral nanographenes

  • Ranran Li,
  • Di Wang,
  • Shengtao Li and
  • Peng An

Beilstein J. Org. Chem. 2023, 19, 736–751, doi:10.3762/bjoc.19.54

Graphical Abstract
  • ]azepine and tetrabromothiophene-S,S-dioxide, followed by oxidative aromatization in the presence DDQ to afford compound 25 in an overall 75% yield. Suzuki−Miyaura cross-coupling reaction of compound 25 with (4-ethylphenyl)boronic acid in the presence of Pd(CH3CN)2Cl2, SPhos, and K3PO4 then furnished the
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Published 30 May 2023

Palladium-catalyzed enantioselective three-component synthesis of α-arylglycine derivatives from glyoxylic acid, sulfonamides and aryltrifluoroborates

  • Bastian Jakob,
  • Nico Schneider,
  • Luca Gengenbach and
  • Georg Manolikakes

Beilstein J. Org. Chem. 2023, 19, 719–726, doi:10.3762/bjoc.19.52

Graphical Abstract
  • slow release of the boronic acid from the aryltrifluoroborates and enables to enantioselectively synthesize of a broader variety of arylglycines, including a common building block for several biologically active compounds. Results and Discussion During our previous studies, we observed that the
  • enantioselectivity of the three-component coupling of glyoxylic acid (employed as its solid, easy-to-handle monohydrate) with 2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-sulfonylamide, and an arylboronic acid was significantly affected by the nature of the boronic acid. Whereas the reaction with phenylboronic acid
  • afforded the Pbf-protected [23] phenylglycine derivative 10a in high yield and enantioselectivity, an almost racemic mixture of 10b was obtained from the corresponding (p-methoxyphenyl)boronic acid (2b, Scheme 2a). This decrease in enantioselectivity can be attributed to a faster racemic background
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Published 25 May 2023

Transition-metal-catalyzed domino reactions of strained bicyclic alkenes

  • Austin Pounder,
  • Eric Neufeld,
  • Peter Myler and
  • William Tam

Beilstein J. Org. Chem. 2023, 19, 487–540, doi:10.3762/bjoc.19.38

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Published 24 Apr 2023

Introducing a new 7-ring fused diindenone-dithieno[3,2-b:2',3'-d]thiophene unit as a promising component for organic semiconductor materials

  • Valentin H. K. Fell,
  • Joseph Cameron,
  • Alexander L. Kanibolotsky,
  • Eman J. Hussien and
  • Peter J. Skabara

Beilstein J. Org. Chem. 2022, 18, 944–955, doi:10.3762/bjoc.18.94

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  • manner similar to [49][50], 4-(2-ethylhexyl)-2-methylthiophene (31), which had been synthesised according to the published literature [47][48][51][52], was lithiated with n-butyllithium, and reacted with trimethyl borate [49][50]. Although a conversion could be detected with TLC, no boronic acid
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Published 01 Aug 2022

Substituent effect on TADF properties of 2-modified 4,6-bis(3,6-di-tert-butyl-9-carbazolyl)-5-methylpyrimidines

  • Irina Fiodorova,
  • Tomas Serevičius,
  • Rokas Skaisgiris,
  • Saulius Juršėnas and
  • Sigitas Tumkevicius

Beilstein J. Org. Chem. 2022, 18, 497–507, doi:10.3762/bjoc.18.52

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  • (tert-butyl)-9H-carbazol-9-yl]-5-methylpyrimidines 2a–d General procedure. 4,6-Bis(3,6-di-tert-butyl-carbazol-9-yl)-5-methyl-2-methylthiopyrimidine (50 mg, 0.072 mmol), the corresponding boronic acid (0.094 mmol), CuMeSal (34 mg, 0.158 mmol), Pd(PPh3)4 (4.2 mg, 0.0036 mmol), Cs2CO3 (46.8 mg, 0.144 mmol
  • , in case of meta-substituted boronic acid, 1 equiv) and dioxane (3 mL) were placed in a screw-cap vial equipped with a magnetic stirring bar and flushed with argon for 10 min. The reaction mixture was heated at 130 °C under stirring for 4 h. Then, dioxane was removed by distillation under reduced
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Published 05 May 2022

Borylated norbornadiene derivatives: Synthesis and application in Pd-catalyzed Suzuki–Miyaura coupling reactions

  • Robin Schulte and
  • Heiko Ihmels

Beilstein J. Org. Chem. 2022, 18, 368–373, doi:10.3762/bjoc.18.41

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  • all, as neither the reaction of 2a with NaIO4 and hydrochloric acid, nor the reaction of 2a with LiOH and subsequent addition of acid (ammonium chloride, hydrochloric acid) gave the desired boronic acid, but led to decomposition, instead. Obviously, the 2-borylated norbornadiene derivatives are acid
  • -labile, so that the synthesis of the boronic acid was not further investigated. In addition, the 4,4,5,5-tetramethyl-2-(3-methylbicyclo[2.2.1]heptadien-2-yl)-1,3,2-dioxaborolane (2b) was obtained by conversion of the known 2-bromo-3-methylbicyclo[2.2.1]heptadiene (1b) [27] to the metalated intermediate
  • catalyst and additive. The 1H NMR-spectroscopic analysis of the reaction showed that in both attempts no reaction occurred. It may be concluded that the nucleophilicity of the boronic ester is not sufficient, however, under the employed conditions, it can be hydrolyzed to the more reactive boronic acid
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Published 01 Apr 2022

Peptide stapling by late-stage Suzuki–Miyaura cross-coupling

  • Hendrik Gruß,
  • Rebecca C. Feiner,
  • Ridhiwan Mseya,
  • David C. Schröder,
  • Michał Jewgiński,
  • Kristian M. Müller,
  • Rafał Latajka,
  • Antoine Marion and
  • Norbert Sewald

Beilstein J. Org. Chem. 2022, 18, 1–12, doi:10.3762/bjoc.18.1

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  • -diaminobutyric acid (Dab), ornithine (Orn), or lysine (Lys). Utilising the Alloc protecting group allowed the coupling of 4-carboxyphenylboronic acid once the linear sequence had been synthesised (Scheme 2C). The intramolecular SMC between 6- or 7-bromotryptophan and the boronic acid afforded the stapled
  • , 1 h. In panel C), amino acids in R1 and R2 are with protecting groups and R2 is resin-bound (Rink amide resin); R3 = 4-phenylboronic acid or (4-ethylphenyl)boronic acid (P2–P5). Supporting Information Supporting Information File 6: Details on the amino acid and peptide synthesis, analytical data of
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Published 03 Jan 2022

Synthesis of highly substituted fluorenones via metal-free TBHP-promoted oxidative cyclization of 2-(aminomethyl)biphenyls. Application to the total synthesis of nobilone

  • Ilya A. P. Jourjine,
  • Lukas Zeisel,
  • Jürgen Krauß and
  • Franz Bracher

Beilstein J. Org. Chem. 2021, 17, 2668–2679, doi:10.3762/bjoc.17.181

Graphical Abstract
  • in nearly quantitative yield according to known protocols [63]. Although O-unprotected hydroxyphenylboronic acids similar to 18 have been reported in the literature [64], we found the synthesis of the more lipophilic O-TBS-protected boronic acid 18 to proceed more facile in a yield of 66% via an
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Published 02 Nov 2021

Recent advances in organocatalytic asymmetric aza-Michael reactions of amines and amides

  • Pratibha Sharma,
  • Raakhi Gupta and
  • Raj K. Bansal

Beilstein J. Org. Chem. 2021, 17, 2585–2610, doi:10.3762/bjoc.17.173

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  • catalytic systems, namely arylboronic acid alone, its dual combination with chiral thiourea and integrated catalyst having boronic acid functionality in the chiral thiourea molecule. The dual combination of arylboronic acid with chiral thiourea was found as effective as arylboronic acid alone for the
  • intermolecular asymmetric Michael addition of alk-2-enoic acids 68 with O-benzylhydroxylamine (69) giving racemic mixture of the product in poor yield. However, the integrated catalyst having boronic acid functionality in the chiral thiourea molecule gave the desired β-benzyloxyamino acid as the single product
  • yields ranged 57–89% with ee 70–97% [52]. A similar chiral multifunctional thiourea/boronic acid was used as an organocatalyst by Michigami et al. for the enantioselective synthesis of N-hydroxyaspartic acid derivatives 76 with perfect regioselectivity and high enantioselectivity (Table 17) [53
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Published 18 Oct 2021

Synthesis of new substituted 7,12-dihydro-6,12-methanodibenzo[c,f]azocine-5-carboxylic acids containing a tetracyclic tetrahydroisoquinoline core structure

  • Agnieszka Grajewska,
  • Maria Chrzanowska and
  • Wiktoria Adamska

Beilstein J. Org. Chem. 2021, 17, 2511–2519, doi:10.3762/bjoc.17.168

Graphical Abstract
  • products was formed. Then, N-2,3-methylenedioxybenzylamino acid 6b and N-3,4,5-trimethoxybenzylamino acid 6c were prepared from boronic acid 5a, glyoxylic acid hydrate (4) and aminoacetals 3b and 3c, in 99% and 90% yield, respectively (Scheme 4). Under the Pomeranz–Fritsch conditions compounds 6b and 6c
  • with 67% yield (53% overall yield from 3d), while the reaction carried out in 20% HCl led to a mixture of products, among which 7f was not detected (Scheme 5). It should be also mentioned that the amino acid 6g with a benzyloxy-substituted aromatic ring, obtained in the Petasis reaction of boronic acid
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Published 07 Oct 2021
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