A NEW IODOVINYL DERIVATIVE OF METHYL PYROPHEOPHORBIDE D OBTAINED VIA TAKAI OLEFINATION REACTION Текст научной статьи по специальности «Химические науки»

Porphyrins

Порфирины

Макрогетзроцикль]

http://mhc-isuct.ru

Paper

Статья

DOI: 10.6060/mhc224669b

A New Iodovinyl Derivative of Methyl Pyropheophorbide d Obtained via Takai Olefination Reaction

Evgeny S. Belyaev,@ and Anastasiya S. Toms

Frumkin Institute of Physical Chemistry and Electrochemistry of the Russian Academy of Scienc es, 119071 Moscow, Russia @Corresponding author E-mail: [email protected]

Modification of chlorin derivatives, which leads to extension of the conjugation chain along the y axis, is the most important direction in the field of natural tetrapyrrole compounds. Iodine-containing derivatives of porphyrins are valuable reagents in such Pd-catalyzed reactions as Suzuki, Mizoroki-Heck, Stille, andSonogashira couplings, as well as Buchwald-Hartwigamination. A new alternative way for functionalization ofC32-position offormyl group of methyl pyropheophorbide d by introducing of iodine has been developed. We have proposed an one-step synthesis of methyl 3-(2-iodovinyl)pyropheophorbide d, including Takai reaction between methyl pyropheophorbide d, iodoform and CrCl2. This junctionalized derivative can be useful for further synthesis of derivatives with n-extending system by Pd-catalyzed cross-coupling reaction.

Keywords: ^lorns, chlorophyll a, tetrapyrrolic compounds, Takai reaction, Pd-catalyzed cross-coupling reactions.

Новое йодвинильное производное метилового эфира пирофеофорбида d, полученное с использованием реакции олефинирования Такаи

Е. С. Беляев,® А. С. Томс

Институт физической химии и электрохимии им.А.Н. Фрумкина Российской академии наук, 119071 Москва, Россия @E-mail: [email protected]

Модификация хлориновых производных, приводящая к увеличению цепи сопряжения вдоль оси у, является важнейшей проблемой в области природных тетрапиррольных соединений. Йодсодержащие порфириновые производные являются ценными реагентами в таких Pd-катализируемых реакциях, как Сузуки, Мизороки-Хека, Стилле, Соногаширы, а также аминировании Бухвальда-Хартвига. В этой статье нами представлена разработка нового альтернативного пути для функционализации формильной группы в С3 2-положении метилового эфира пирофеофорбида dчерез введение атома йода. Таким образом, был предложенодностади й-ный синтез метилового эфира 3-(2-иодвинил)пирофеофорбида а, который включал в себя реакцию Такаи метилового эфира пирофеофорбида d с йодоформом и СгС12. Йодвинильное производное открывает широкие возможности для синтеза производных с расширенной п-системой через его использование в Pd-катализируемых реакциях кросс-сочетания.

Ключевые слова: Хлорины, хлорофилл а, тетрапиррольные соединения, реакция Такаи, Pd-катализируемые реакции кросс-сочетания.

Introduction

Natural and synthetic tetrapyrrole compounds are widely used in medicine, mainly as drugs for photodynam-ic therapy (PDT) of cancer[1] and as agents for antimicrobial PDT.[2] They are also used to create materials for solar energy.[3,4] Based on their metal complexes, oxygen and p H

sensitive sensors are being developed.[5-10] Often, in the field of porphyrin chemistry, the main goal is to improve and impart certain optical, biological, or photophysical properties to the macrocycle. However, obtaining a molecule with the desired properties is not always an easy task. In this regard, there is a need for simple and accessible methods for the functionalization and modification of

tetrapyrrole macrocycles. For chlorophyll a derivatives, in particular for phorbine ones, the most important characteristics are the intensity and position of the long-wavelength band Qy, which significantly affects molecule optical prop-erties.[11] The position of the Qy band in the electronic absorption spectra depends on the nature and type of binding of the substituents located along the y axis of the macrocycle. The introduction into the C3 and C13 positions of the methyl pyropheophorbide a, unsaturated substituents conjugated with the 18-n electronic system of the tetrapyrrole ring is know n to had to a bathochromic shift of the Qy absorption band whose value depends on the donor or acceptor strength of the substituent.[12] However, methods allowing for the introduction of various substituents with a simultaneous increase of conjugation chain are very rare, and their development is one of the scientific directions of our research group.

Currently, in organic and bioorganic chemistry, extremely popular modification methods are Pd-catalyzed cross-coupling reactions, which allow one to obtain various complex molecules gently and with high yield.[13] The efficiency and relevance of cross-coupling reactions in the chemistry of tetrapyrrole compounds are also evident from the available publications.!14-18! However, in contrast to the great number of publications on the modification of por-phyrins by Pd-catalyzed reactions, little attention has been paid to the development and study of similar approaches to the functionalization and modification of natural chlo-rins.[19,20] One of the most important reagents in such reactions as Suzuki, Mizoroki-Heck, Buchwald-Hartwig amination, Stille and Sonogashira coupling, etc., are halogen derivatives, which makes the direct halogenation of some positions of the chlorin macrocycle a very actual task. The introduction of a halogen atom into the macrocycle is possible via the Takai olefination.[21] The reaction mechanism has been studied and described in detail.[22] The main advantage of this reaction is its stereoselectivity, leading to the formation only of the ^-configuration of the resulting double bond.

Experimental

General

Reactions were carried out under argon atmosphere, using commercially available reagents that were purchased and used as received. Starting methyl pheophorbide a was obtained from commercial sources. Heating reaction vessels was performed with oil bath. Column chromatography was performed using 40-63 |m silica gel, preparative thin layer chromatography (TLC) was performed using glass plates coated with 5-40 |im silica gel (5 mm thick). Control of the reactions was provided by TLC using aluminum-backed Silica Gel 60 F254 pre-coated plates. 1H and 13C NMR spectra were recorded with a Bruker Avance III 600 MHz spectrometer at room temperature in CDCl3. Chemical shifts are reported relative to signals of residual protons of solvents (CDCl3 - 7.26 ppm). Mass spectra were recorded with UltrafleXtreme mass spectrometer (Bruker Daltonics) in a positive-ion mode using reflection mode with 20 MV voltage without matrix. Electronic absorption spectra were recorded with U-2900 (Hitachi) spectrophotometer in quartz rectangular cells of 10 mm path length at concentration 10-5 M in CH2Cl2.

Synthesis

Preparation for Takai reaction: The reactions conducted under anhydrous conditions, glassware was dried 10 min in an

oven at 250-300 °C. Commercial CrCl2 was also dried under 150200 °C for 10 min. Reactions were carried out under an atmosphere of argon. THF for Takai reaction was dried over Na and with benzophenone as indicator.

Preparation of 0.9810-3 M OsO4 solution. Cleaned of external contaminants a sealed ampoule containing 250 mg of OsO4 was placed and broken into an Erlenmeyer flask with 100 mL of absolute methylene chloride. The flask contents were thoroughly mixed, after that the solution was ready for use.

Zn11 complex of methyl pyropheophorbide d (8) was synthesized from the corresponding free base 7 via the standard procedure described in.[23] A methanol solution (1 mL) saturated with Zn(OAc)2 2H2O was added to a dichloromethane solution (10 mL) of free base 7 (10 ^mol) and stirred at room temperature overnight. The reaction mixture was poured into aqueous 4% NaHCO3 and extracted with dichloromethane. The organic layer was washed with water, dried over Na2SO4 and filtered. After the solvent was evaporated, the residue was purified with recrystallization from dichloromethane and ethanol to give the corresponding zinc complex 8 which can be used without additional purification.

Methyl pyropheophorbide a (1)[24] was obtained using a known procedure.'25' Methyl pheophorbide a (1 g) was dissolved in pyridine (80 mL). The mixture was stirred for 2 days at reflux in an oil-bath at 140-160 °C. Then the solvent was thoroughly concentrated in vacuo. The residue was diluted with CH2Cl2 and extracted with water. The organic phase was dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography in a CH2Cb/EtOH system (1:100) followed by recrystallization from CH2Cl2 and hexane to give 0.82 g of methyl pyropheophorbide a 1. Yield: 91%. 'H NMR (CDCb) 5 ppm: 9.40 (1H, s, 10-H) 9.43 (1H, s, 5-H),

8.58 (1H, s, 20-H), 8.04 (1H, q, J = 11.4 Hz, J = 17.7 Hz, 31-H), 6.32 (1H, d, J = 17.7 Hz, 32-H), 6.21 (1H, d, J = 11.4 Hz, 32-H), 5.29 (1H, d, J = 19.3 Hz, 132-Ha), 5.12 (1H, d, J = 19.3 Hz, 132-Hb), 4.52 (1H, q, J = 7.5 Hz, 18-H), 4.33 (1H, m, 17-H), 3.72 (2H, q, J = 7.8 Hz, 8>-CH2), 3.71 (3H, s, 12-CH3), 3.64 (3H, s, 172-CO2CH3), 3.44 (3H, s, 2-CH3), 3.28 (3H, s, 7-CH3), 2.73 (1H, m, 171-Ha), 2.59 (1H, m, 172-Ha), 2.33 (2H, m, 171-Hb, 172-Hb), 1.84 (3H, d, J = 7.5 Hz, 18-CH3), 1.73 (3H, t, J = 7.8 Hz, 82-CH3), 0.10 and -1.64 (2H, each s, NHx2). UV-Vis (CH2O2) X nm (Arel.): 413 (1.00), 508 (0.10), 539 (0.08), 609 (0.07), 667 (0.44).

Methyl pyropheophorbide d (7) was obtained by oxidation of methyl pyropheophorbide a 1 with OsO4/NaIO4 system.'26' To a solution of methyl pyropheophorbide a (100 mg , 0.18 mmol) in THF (25 mL) at 0 °C was added 0.0098 M solution of OsO 4 in anhydrous CH2Cl2 (0.4 ^L) and 0.11 M solution of NaIO4 in H2O (10 mL). The mixture was stirred overnight at room temperature. The progress of the reaction was monitored by UV-Vis spectros-copy. The residue was diluted with CH2Cl2 and extracted with a water solution of Na2S2O3 and then with water. The organic phase was dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The reaction product did not require further purification. Yield: 95 mg (96 %). 'HNMR (CDCb)5 ppm: 11.52 (1H, s, 3'-H), 10.22 (1H, s, 10-H), 9.53 (1H, s, 5-H), 8.83 (1H, s, 20-H), 5.35 (1H, d, J = 19.6 Hz, 132-Ha), 5.20 (1H, d, J = 19.6 Hz, 132-Hb),

4.59 (1H, m, 18-H), 4.40 (1H, m, 17-H), 3.77 (3H, s, 12-CH3), 3.68 (5H, m, 8*-CH2 and 172-CO2CH3), 3.65 (3H, s, 2-CH3), 3.27 (3H, s, 7-CH3), 2.76 (1H, m, 17*-Ha), 2.63 (1H, m, 172-Ha), 2.34 (2H, m, 171-Hb, 172-Hb), 1.88 (3H, d, J = 7.3 Hz, 18-CH3), 1.71 (3H, t, J = 7.7 Hz, 82-CH3), -0.16 and -2.13 (2H, each s, NH x 2). UV-Vis (CH2Cl2) \ nm (Arel.): 496 (1.00), 521 (0.13), 555 (0.14), 636 (0.08), 695 (0.72).

(E)-3-(2-Iodovinyl)pyropheophorbide d methyl ester (10). A 25 mL Schlenk 's flask was charged with a stir bar and CrCh (166 mg, 0.0014 mol, 8.6 equiv) and dried under 150-200 °C and in vacuo for 10 min. It was then stoppered and flushed with argon. Anhydrous THF (5 mL) was added and the suspension was cooled to -5 °C with stirring and bubbled through with argon. CHI3 (164 mg, 0.4 mmol, 2.5 equiv) and Zn(II) complex of methyl pyropheophorbide d (100 mg, 0.16 mmol, 1 equiv) were dis-

solved in 10 mL of anhydrous THF and added to the THF/CrCk suspension dropwise. The reaction was stirred for 3 h under argon, as a deep green solution with suspended chromium. Then the solvent was concentrated in vacuo. The residue was diluted in a minimum amount of CH2Q2 and stirring with 1 mL of 37 % HCl for 2 min. The reaction mixture was then diluted with CH2Q2 and extracted with a water solution of NaHCO3 and then with water. The organic phase was dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude product was purified by preparative TLC in a CH2Cl2/EtOH system (100:4) followed by recrys-tallization from CH2Cl2 and hexane to give 54 mg of (E)-3-(2-iodovinyl)pyropheophorbide d methyl ester 10. The reaction overall yield is 49 %. 1H NMR (CDCl3) Sh ppm: 9.53 (1H, s, 10-H), 9.25 (1H, s, 5-H), 8.71 (1H, d, J = 15.0 Hz, 3'-H), 8.60 (1H, s, 20-H), 7.40 (1H, d, J = 15.0 Hz, 32-H), 5.29 (1H, d, J = 19.2 Hz, 132-Ha), 5.14 (1H, d, J = 19.2 Hz, 132-Hb), 4.53 (1H, m, 18-H), 4.34 (1H, m, 17-H), 3.70 (5H, m, 12-CH3 and 8'-СШ), 3.64 (3H, s, 172-CO2CH3), 3.37 (3H, s, 2-CH3), 3.25 (3H, s, 7-CH3), 2.73 (1H, m, 17'-Ha), 2.59 (1H, m, 172-Ha), 2.33 (2H, m, 17'-Hb, 172-Hb), 1.84 (3H, d, J = 7.4 Hz, 18-CH3), 1.72 (3H, t, J = 7.8 Hz, 82-CH3), 0.29 and -1.85 (2H, each s, NH x 2). 13C NMR (CDCls) Sc ppm: 196.1 (C13'(>C=O), 173.4 (C173(>C=O), 171.2 (C19), 160.7 (C16), 154.9 (C6), 151.0 (C9), 149.0 (C14), 145.1 (C8), 140.8 (C1), 138.2 (C11), 137.5 (C3'(-CH=), 136.2(C7), 135.3 (C4), 134.9 (C3), 131.2 (C12), 130.8 (C2), 128.8 (C13), 106.3 (C15), 104.1 (C10), 97.0 (C5), 93.3 (C20), 83.3 (C32), 51.8 (C17), 51.7 (C174(-OCH3), 49.9 (C18), 48.1 (C132), 31.0 (C172), 29.9 (C171), 23.2 (C18'(-CH3), 19.5 (C81 (-CH2), 17.4 (C82(-CH3), 12.3 (C2'(-CH3), 12.1 (C12'(-CH3), 11.3 (C7'(-CH3). MS (SALDI): m/z found 673.1, 674.1, 675.1 calcd. for C34H35IN4O3: [M]+, 673.18; 13C12C33H35IN4O3: [M]+, 674.18; 13C212C32H35IN4O3: [M]+, 675.18. UV-Vis (СШСк) X nm (Arel.): 418 (1.00), 511 (0.12), 541 (0.11), 615 (0.10), 674 (0.42).

Results and Discussion

Recently, we have shown two-step regioselective one-pot bromination of vinyl group of methyl pyropheophorbide a and examined its reactivity in Pd(0)-catalyzed cross coupling reactions.[19] Moreover, our research group has examined bromovinyl derivative of methyl pyropheophorbide a as a reagent in Suzuki-Miyaura reaction, resulted in the formation of methyl ester (E)-32-(4,4,5,5-tetramethyl-

1,3,2-dioxDborolan-2-yl) pyropheophorbide a, a useful compound for further synthesis of п-extended macroheter-ocyclic systems (Scheme 1).[20]

In this article we have developed a new approach for modification of C3-position of methyl pyropheophorbides, allowing to significantly increase the yield of C3-substituted methyl pyropheophorbide a derivatives. Generally, we proposed a method for introducing the iodine atom in C32-position of methyl pyropheophorbide d to obtain (E)-3-(2-iodovinyl)pyropheophorbide d methyl ester. As a raw material we used methyl pyropheophorbide a which, according to a well-known method,[26] was converted to corresponding methyl pyropheophorbide d. First, the Takai reaction was carried out on a free base of methyl pyrophe-ophorbide d, however, this pathway led to the formation of a large number of by-products that could not be separated. To prevent side reactions at nitrogen atoms in the macrocycle ring, metalation of chlorin 7 was carried out using zinc(II) acetate. Zinc complex 8 was further introduced into the Takai reaction using a large excess of CrCl2 (8.6 equiv) and 2.5 equiv CHI3 in absolute THF under argon atmosphere. Since zinc complex 9 is unstable under the conditions of chromatography on silica gel, after the reaction, in situ demetalation was carried out with concentrated HCl. As a result, the desired product was obtained with a total yield of 47 % (Scheme 2).

The structure of the resulting iodovinyl derivative 10 was confirmed by NMR spectroscopy (Figure 1). In the 1H NMR spectrum, we observed the disappearance of the formyl group proton and formation of two characteristic doublets, which indicates the AX spin system formation. The double bond has E-configuration which is confirmed by coupling constant J = 15.0 Hz of the 3-iodovinyl group protons. Signal at 83.3 ppm in the 13C NMR spectrum (Figure 2) belongs to the iodine substituted vinylic carbon atom, the high field shift of which is due to the heavy atom effect of iodine atom, while C31 atom possesses low field shift possibly due to the higher mesomeric effect of iodine atom compared to the corresponding bromine substituted vinyl group in 2.

Scheme 1. Different ways for modification C3-position of pyropheophorbides. i: Br2, -90C, CH2CI2; ii: 80 C; iii: a - Pd0, base, tribu-ty l(vinyl)tin, b - Pd0, base, phenylboronic acid, c - Pd0, base, methyl acrylate; iv: MeOH, Zn(OAc)2; v: B2pin2, Pd(PPh3)i, Cs2CO3, 1,4-dioxane; vi: a - PdCl2(CH3CN)2, dppp, Cs2CO3, 1,4-dioxane, iodobenzene; b - Pd(PPh3)4, Cs2CO3, 1,4-dioxane, 1-iodo-3-nitrobenzene, c - Pd(PPh()4, Cs2CO3, 1,4-dioxane, 4-iodophenol, d - Pd(PPh3)4, Cs2CO3, 1,4-dioxane, 4-iodoacetophenon, e - Pd(PPh3)4, Cs2CO3, 1,4-dioxane, 4-iodotoluene.

MeO.

CHIa/CrCI, THF * H

Zn(OAc)2 x 2H2or 7: M = 2H MeOH L~8: M = Zn

MeCV

r 9: M = Zn

HCI

U-10: M = 2H

Scheme 2. Synthesis of (£)-3-(2-iodovinyl)pyropheophorbide d methyl ester using Takai reaction.

Figure 1. Fragment of 'H NMR spectrum of (,E)-3-(2-iodovinyl)pyropheophorbide d methyl ester.

We believe that such moderate reaction yield is associated with a steric factor, as well as a multi-stage metalation - demetalation process, leading to losses at all stages of the proposed protocol. However, iodine derivatives are known to be significantly more effective in the Pd-catalyzed reactions than the corresponding bromine and chlorine derivatives.'27-30! For this reason, the resulting iodovinyl derivative 10 is expected to be more active than it bromvinyl analog 2. This suggests further research to optimize this approach.

Conclusions

In conclusion, a new method for synthesis of a halo-genated derivative - (E)-3-(2-iodovinyl)pyropheophorbide

d methyl ester has been elaborated. This strategy included 4 stages: the stage of oxidation of the vinyl group, metalation, Takai reaction and demetalation. Takai reaction occurs with 100 % stereoselectivity, and the double bond has E-configuration, which is confirmed by coupling constant J = 15.0 Hz of the 3-iodovinyl group protons. The developed approach opens up a broad possibility for introduction of numerous aromatic and unsaturated substituents along the y-axis of the macrocycle to form extended n-conjugated chlorin systems.

Acknowledgements. This work was supported by President Grant for Government Support of Young Russian Scientists (No. MK-586.2022.1.3).

Figure 2. Fragment of *H-13C HSQC spectrum of compound 10. Right inset: 13C NMR shifts value of C31 and C32 carbon atoms of variously substituted vinyl groups showing the influence iodine atom on the carbon signals.

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Received 20.09.2022 Accepted 26.10.2022