Visible Light-Promoted Amide Bond Formation via One-Pot Nitrone in Situ Formation/Rearrangement Cascade

Open AccessCCS ChemistryRESEARCH ARTICLE1 Nov 2021Visible Light-Promoted Amide Bond Formation via One-Pot Nitrone in Situ Formation/Rearrangement Cascade Bao-Gui Cai, Shuai-Shuai Luo, Lin Li, Lei Li, Jun Xuan and Wen-Jing Xiao Bao-Gui Cai Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials, Key Laboratory of Functional Inorganic Materials of Anhui Province, College of Chemistry and Chemical Engineering, Anhui University, Hefei, Anhui 230601 Google Scholar More articles by this author , Shuai-Shuai Luo Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials, Key Laboratory of Functional Inorganic Materials of Anhui Province, College of Chemistry and Chemical Engineering, Anhui University, Hefei, Anhui 230601 Google Scholar More articles by this author , Lin Li Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials, Key Laboratory of Functional Inorganic Materials of Anhui Province, College of Chemistry and Chemical Engineering, Anhui University, Hefei, Anhui 230601 Google Scholar More articles by this author , Lei Li Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials, Key Laboratory of Functional Inorganic Materials of Anhui Province, College of Chemistry and Chemical Engineering, Anhui University, Hefei, Anhui 230601 Google Scholar More articles by this author , Jun Xuan *Corresponding authors: E-mail Address: [email protected] E-mail Address: [email protected] Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials, Key Laboratory of Functional Inorganic Materials of Anhui Province, College of Chemistry and Chemical Engineering, Anhui University, Hefei, Anhui 230601 Key Laboratory of Structure and Functional Regulation of Hybrid Materials, Ministry of Education, Anhui University, Hefei, Anhui 230601 Google Scholar More articles by this author and Wen-Jing Xiao *Corresponding authors: E-mail Address: [email protected] E-mail Address: [email protected] Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, Hubei 430079 Google Scholar More articles by this author https://doi.org/10.31635/ccschem.020.202000588 SectionsSupplemental MaterialAboutAbstractPDF ToolsAdd to favoritesDownload CitationsTrack Citations ShareFacebookTwitterLinked InEmail A green and sustainable synthetic strategy for amide bond formation utilizing a visible light-promoted nitrone formation/rearrangement cascade was developed. This method utilized visible light as the sole and clean energy source without the need for an exogenous photoredox catalyst or additive. Moreover, nitrones are generated in situ, bypassing the isolation process and producing only nitrogen gas as a byproduct. The synthetic value of this protocol has potential applications in the syntheses of amides containing important natural products and drug-based complex molecules. Download figure Download PowerPoint Introduction The amide bond is a fundamental and important structural motif not only because it is a key chemical connection in proteins but it is also found in many insecticides, pharmaceutical agents, polymers, and some fine chemicals.1–5 Consequently, a great deal of effort in both industry and academia has been devoted to developing facile approaches for amide synthesis. Generally, the direct condensation of amines and carboxylic acids is the most straightforward method for amide synthesis due to readily available and inexpensive starting materials (Scheme 1a).6,7 However, this method requires the use of stoichiometric amounts of activating reagents, so the process suffers from poor atomic economy.8–12 Meanwhile, “nonclassical” amide syntheses using carboxylic acid or amine surrogates have also been recently established.13,14 Note that “amide formation avoiding poor atom economy reagents” was identified as a top priority area in a 2007 round table devoted to key green chemistry research areas in organic chemistry.15 Based on this consideration, it is still desirable to develop green and sustainable methods for the formation of amide bonds. Scheme 1 | (a and b) Amide bond formation through condensation reaction and photochemical rearrangement of nitrones. Download figure Download PowerPoint Nitrones are highly useful synthons in synthetic organic chemistry and have been widely used as electrophiles, radical acceptors, or three-atom cycloaddition partners.16–24 Thus far, there has been little exploration of the photochemical transformation of nitrones. During the 1950s, Splitter et al. found that irradiation of nitrones under UV light triggered their rearrangement to form oxaziridines,25 and further opening of oxaziridines to amides (Scheme 1b).26 However, photopromoted rearrangement of nitrones into amides via a one-pot reaction has not been reported often.27–30 In 2013, the Jamison group31 demonstrated a photopromoted rearrangement of nitrones under continuous-flow conditions and provided a very general approach for amide bond formation. This reaction not only represented a novel and useful method for peptide fragment coupling but also expanded the scope of protein synthesis. However, the reaction required high-energy UV light and the nitrone substrates in all previously reported cases needed to be presynthesized. To the best of our knowledge, direct in situ rearrangement of nitrones to amides using only visible light irradiation without the need for an exogenous additive or photoredox catalyst is still unknown. Chemical reactions initiated using visible light as a green energy source have had a profound effect on the creation of unique reaction manifolds in organic synthesis that were previously difficult or unavailable to realize using traditional thermal approaches.32–41 Pioneering work by Jurberg and Davies42 revealed that aryldiazoacetates undergo photolysis efficiently to give reactive carbene singlet species under visible light. Due to the zwitterionic nature of the photogenerated singlet carbene, various nucleophilic atoms readily trap the electrophilic singlet carbene intermediate. Shortly after this discovery, many groups investigated visible light-promoted carbene generation/functionalization reactions from aryldiazoacetates, such as C–H/X–H insertion, cyclopropanation, cyclopropenation, and the Doyle–Kirmse reaction.43–54 Motivated by these findings and our continuing research interests in the development of visible light-promoted useful chemical transformations,45–57 we speculated that nitrosoarene 2 might effectively trap carbenes.58–63 As depicted in Scheme 1, photogenerated carbene species from aryldiazoacetate 1 reacts with nitrosoarene 2 via its more nucleophilic N-center to give nitrone 3. The large, conjugated, π-system of 3 results in a visible light absorbance spectrum which triggers the subsequent rearrangement of 3 to amide 4 under visible light. This one-pot photocascade amide bond formation process has several advantages, including: (1) visible light utilization as the sole, clean energy source without the need for an exogenous photoredox catalyst or additive; (2) nitrones generated in situ, bypassing the isolation process; and (3) harmless nitrogen gas is the sole byproduct. Experimental Methods Typical procedure for the reaction ( 4aa as an example): to a 10 mL Schlenk flask equipped with a magnetic stir bar, 1a (0.3 mmol), 2a (0.1 mmol), and dry tetrahydrofuran (THF) (1.0 mL) were added. The resulting mixture was degassed via a “freeze–pump–thaw” procedure (three times). After the solution was stirred at a distance of ∼3 cm from a 24 W blue light-emitting diode (LED) at room temperature for 12 h, the solvent was removed by vacuum and the crude product was purified by flash chromatography on silica gel: 200–300; eluant: petroleum ether/ethyl acetate (20∶1 to 5∶1) to provide pure product 4aa as yellow oil in 83% yield. Proton nuclear magnetic resonance (1H NMR) (400 MHz, CDCl3, 300 K, δ) (ppm): 7.72 (m, 1H), 7.70 (t, J = 1.7 Hz, 1H), 7.52–7.48 (m, 1H), 7.42 (m, 4H), 7.37–7.32 (m, 1H), 7.26 (d, J = 1.4 Hz, 1H), 7.24 (dd, J = 1.6, 1.1 Hz, 1H), 3.67 (s, 3H). Carbon nuclear magnetic resonance (13C NMR) (100 MHz, CDCl3, 300 K, δ) (ppm): 172.06, 155.19, 138.60, 135.55, 131.99, 129.26, 128.34, 128.27, 128.04, 127.93, 53.81. High-resolution mass spectrometry (HRMS) [electrospray ionization (ESI)] exact mass: [M + H]+calcd for C15H13NO3: 256.0974; found: 256.0989. Results and Discussion Initially, the hypothetical, in situ formed, nitrone 3aa was presynthesized, and the UV–vis absorbance spectra of aryldiazoacetate 1a, nitrosobenzene 2a, and nitrone 3aa were investigated. As shown in Figure 1a, for materials 1a and 2a, only phenyldiazoacetate 1a absorbed in the visible region (Figure 1a, red line) and may be attributed to a decrease in the n–π* energy gap transition of the diazo group when an aryl donor group is introduced.43,44 In a positive way, nitrone 3aa also absorbed in the visible region, which indicated that 3aa might be activated for further rearrangement by absorption of visible light (Figure 1a, blue line). To test this hypothesis, we carried out the reaction of 1a and 2a in degassed THF under irradiation using 24 W blue LEDs (Figure 1b). We were pleased to find the targeted amide 4aa was obtained in 83% yield after irradiation for 12 h. A control experiment confirmed the desired amide did not form without blue LED irradiation (for details, see the Supporting Information). Figure 1 | (a) UV–vis absorbance analysis of aryldiazoacetate 1a, nitrosobenzene 2a, and the corresponding nitrone 3aa. (b) Reaction of 1a and 2a under the irradiation of 24 W blue LEDs at room temperature in THF. Download figure Download PowerPoint After optimizing the reaction conditions, we investigated the scope of this blue LED-promoted amide formation by reacting various aryldiazoacetates 1 with nitrosobenzene 2a. As revealed in Table 1, the reaction generally proceeded well to give the desired amides in moderate to good yields. Both electron rich (–Me and –OMe) and electron deficient (–F, –Cl, and –Br) groups were incorporated at the para positions on the phenyl ring of aryldiazoacetate 1, which led to the corresponding amides 4ba– 4fa in yields from 49–73%. However, aryldiazoacetate 1e, with a strong electron-withdrawing –CF3 group, failed to yield 4ga. Note that meta- and di-substituted aryldiazoacetates were also amenable substrates ( 4ha–4ja). Furthermore, aryldiazoacetates containing different reactive functional groups, such as an alkene ( 4ka), an alkyne ( 4la), and an ester ( 4ma), underwent the desired amide formation with high efficiency. No intramolecular cyclopropanation or cyclopropenation products were observed in cases of substrates containing unsaturated carbon–carbon double or triple bonds. A naphthyl ring was also tolerated ( 4na). We turned our attention to substituent modification of the ester group in aryldiazoacetates. We found that replacement of the methyl group in 1a with other primary alkyl groups ( 1o and 1p), secondary alkyl group ( 1q), cyclic alkyl groups ( 1r and 1s), or primary alkyl groups containing sensitive alkenes ( 1t), alkynes ( 1u), or ethers ( 1v) all successfully yielded the corresponding amides 4oa– 4va in good to excellent yields (72–99%). Table 1 | Substrate Scopea,b aReaction conditions: Reaction performed with 1 (0.3 mmol) and 2 (0.1 mmol) in dry THF (1.0 mL) at r.t. under irradiation with 24 W blue LEDs for 12 h. bIsolated yield. Next, the reaction scope was examined with respect to the nitrosoarene 2 component and those results are shown in Table 1. Under optimized reaction conditions, various para-alkyl ( 2b, 2i, and 2j), alkoxyl ( 2k), aryl ( 2e), and halogen ( 2c, 2d, and 2f– 2h)-substituted nitrosoarenes reacted well with phenyldiazoacetate 1a. Regarding reaction efficiency, better results were obtained for para-substituted nitrosoarenes as compared with ortho-substituted substrates and may be due to steric effects ( 4ad and 4ag). The structure of amide 4ae was unambiguously confirmed by X-ray diffraction (CCDC 2023886). Notably, nitrosoarenes bearing ketone, ester, or free alcohol fragments were well tolerated and afforded amides 4al– 4an in moderate yields. Also, 2-nitrosopyridine ( 2o), nitroso compounds that contained electron rich nitrogen atoms, for example, 2p and 2q, and 2-methyl-2-nitrosopropane ( 2r) failed to give the final amides. To further highlight the application potential of this visible light-promoted amide formation protocol, we treated useful natural products and drug-derived complex molecules (Table 2) with this synthetic strategy. Natural isolates l-(−)-Borneol, Citronellol, l-Menthol, and Pterostilbene were successfully converted into amides 5– 8 in high yields (69–85%). Gemfibrozil and Propofol also reacted and gave the corresponding drug-modified amides 9 and 10 with 99% and 82% yields, respectively. Table 2 | Synthesis of Amides Containing Some Natural Isolates and Biological Frameworksa,b aReaction condition: Reaction performed with 1 (0.3 mmol) and 2 (0.1 mmol) in dry THF (1.0 mL) at r.t. under irradiation with 24 W blue LEDs for 12 h. bIsolated yield. To show the utility and practicality of this method, some useful synthetic applications of final amide products were investigated. As shown in Scheme 2a, a copper-catalyzed click reaction introduced an important triazole moiety to produce 4ua in a 91% yield. Treatment of 4qa under EtOH/KOH successfully yielded Propham, a pre- and post-emergent herbicide for the control of weeds, in 83% yield (Scheme 2b).64,65 More significantly, a straightforward, three-step, total synthesis of Amaryllidaceae alkaloid Trispheridine from 4aa was achieved in 54% overall yield (Scheme 2c).66,67 Scheme 2 | (a–c) Synthetic transformations. Download figure Download PowerPoint Several control experiments were carried out to glean insight into the reaction mechanism (Scheme 3). A similar yield of amide 4aa obtained when 1.0 equiv of radical scavenger TEMPO (2,2,6,6-tetramethyl-1-piperinedinyloxy) was added to the model reaction indicated that the transformation may not involve a radical pathway (Scheme 3a). Ethyl diazoacetate 12 is an efficient carbene trapping reagent under photochemical conditions.45 When 1.0 equiv of 12 was added as a trapping reagent, the reaction afforded 4aa in 75% yield, together with a 36% yield of alkene 13, which suggested the carbene species formed during the reaction (Scheme 3b). Shortening the reaction time to 6 h, we isolated the nitrone intermediate 3aa in 69% yield (Scheme 3c). Treatment of 3aa under standard reaction conditions provided the desired amide 4aa in excellent yield; control experiments revealed that light irradiation was essential for amide product formation (Scheme 3d). Note that, no reaction occurred when 3aa was performed in dark condition at room temperature or 50 °C. Scheme 3 | (a–e) Mechanism studies. Download figure Download PowerPoint Based on these experimental results and previous literature reports,43–54 a plausible mechanism is proposed in Scheme 3e. Initially, visible light irradiation of aryldiazoacetate resulted in N2 gas extrusion and generated a reactive carbene species. The carbene species reacted with a nitrosoarene via its nucleophilic N-center to give the zwitterion intermediate 14, which converted the more stable nitrone 3aa as the predominant resonance form. Under the same blue LED irradiation, 3aa further converts to oxaziridine 15,25 which subsequently rearranges to the final amide product 4aa. The Gibbs free energy of the formation of 4aa is 27.9 kJ/mol lower than that of the phenyl migration product under the theoretical level of M062x/cc-pvtz, which suggests migration of an ester group is thermodynamically favorable to a phenyl group (see the Figures S1–S3 and Tables S1–S3 in Supporting Information). Conclusions We developed a green and sustainable amide synthetic pathway using a visible light-promoted, one-pot, nitrone formation/rearrangement cascade. This method showed excellent substrate scope and functional group tolerance for both aryldiazoacetate and nitrosoarene components. Compared with reported photopromoted nitrone rearrangements, this method utilized only visible light as the sole and clean energy source without the need for an exogenous photoredox catalyst or additive. Moreover, nitrones are generated in situ, bypassing the isolation process, and producing only nitrogen gas as a byproduct. We anticipate this one-pot amide formation strategy will find further applications in photochemical syntheses as well as biomolecular studies. Supporting Information Supporting information is available and includes the general information, experimental methods, detail descriptions, and copies of NMR spectra for products. Conflict of Interest There is no conflict of interest to report. 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