2020-03-04 10:19:08
Erfei Wang,[a] Jiawei Zhang,[b] Zhuoran Zhong,[a] Kaixuan Chen,[a] and Mao Chen*[a]
Dedicated to Professors Stephen L. Buchwald and John F. Hartwig for celebration of the receipt of the 2019 Wolf Prize in Chemistry
1.Introduction
Transition-metal-catalyzed cross-coupling reaction has become one of the most powerful transformations in organic synthesis for the carbon-carbon bond formation. For example, named reactions including Suzuki-Miyaura,[1] Sonogashira,[2] Heck,[3] Hiyama[4] and Stille[5] reactions have revolutionized avenues to access organic molecules. These homogeneous catalytic processes have been extensively used in both academic and industrial fields,[6] providing important compounds including pharmaceuticals,[7] agrochemicals,[8] natural products,[9] poly- mer materials[10] and so on.[11]
Given the increasing concerns of sustainable development and production costs (i.e., catalyst, purification), many efforts have been devoted to improve the recyclability of catalysts and/or reduce the amount of transition-metal catalysts.[12] Consequently, the development of transition-metal catalysis has been accompanied with the evolution and upgrading of ligands,[13] which has enabled homogeneous catalysis with decreased catalyst usages, improved activity and selectivity, as well as expanded substrate scopes.[14] However, the application of homogeneous catalytic processes could be influenced by concerns of transition-metal contaminations. In this regard, heterogeneous transition-metal-catalyzed cross-couplings based on polymeric, inorganic and other carrying materials have been developed to simplify the purification process and reduce the catalyst cost.[15] A combination of the high activity of homogeneous catalysis and the ease in post-process of heterogenous catalysis would be desirable for the cross- coupling reactions.
Recently, we demostrated a highly efficient and low- catalyst-loading Pd-catalyzed Suzuki Miyaura cross-coupling method with a polymeric monophosphine ligand, “WePhos”, enabling rapid catalsyt shuttling, simple catalyst seperation and continuous catalyst-recycling synthesis under biphasic conditions (Scheme 1).[16] However, when further efforts were taken to extend the application scope of WePhos in other C-C bond forming cross-couplings, lower reactivities were ob- served, even at higher catalyst loadings. In this work, inspired by the elegent design of biaryldialkyl phosphine ligands,[17] we developed a poly(ethylene glycol) (PEG) linked ortho-MeO- phenyldicyclohexylphosphine ligand, “MeO-WePhos”, which allows extending the efficient shuttling catalysis to Pdcatalyzed cross-couplings inlcuding Sonogashira, Heck, Hiya- ma and Stille reactions as regulated by temperature.
2. Results and Discussion
The thermoresponsive polymeric ligand 4 a MeO-WePhos5000 (number average molecular weight (Mn) of PEG is 5000 g/ mol) was synthesized at 79 % overall yield following the synthetic route summarized in Scheme 2. The structure of 4 a was analysed with matrix-assisted laser desorption/ionization- time of flight (MALDI-TOF) mass spectrometry. As shown in Figure 1a, a single set of peaks for phosphine ligand 4 a is observed in the MALDI-TOF mass spectrum, and the differ- ence value of two neighbouring peaks equals the molar mass of a single repeating unit (m/z = 44.05, Figure 1b) in PEG. The absolute value of m/z is in accord with the molecular weight calculated by the MALDI-TOF result of 4 a. In Figure 1c, the y-intercept of m/z versus the corresponding number of repeating units demonstrates that the molecular weight of the chain-end group in 4 a was consistent with the expected value. Measurements with proton nuclear magnetic resonance (1 H NMR), 31 P NMR ( 9.41 ppm) and size-exclusion chroma- tography (SEC) further confirm the precise chemical structure of the phosphine ligand MeO-WePhos5000 (Figures S1).
With the same synthetic route, the WePhos5000 4 b[16] and PPh3-PEG5000 4 c[18] were prepared at 83 % and 87 % overall yields, respectively. The structures of 4 b and 4 c were also confirmed by MALDI-TOF mass spectra (Figures S2c–S2d), NMR spectra and other measurements.
Sonogashira reaction is among the most useful methods to synthesize conjugated (hetero)arynes via the cross-coupling of terminal alkynes and aryl halides.[19] The polymeric ligands from 4 a to 4 c were employed in the Pd-catalyzed Sonogashira cross-coupling reaction of bromobenzene and phenylacetylene using potassium carbonate (K2CO3) as the base at 90 °C in water/toluene (v/v = 4/1). As shown in Figure 2, the reaction with 4 a provided the highest yield (99 %) in 6 h reaction time as determined by gas chromatography (GC) (90 % and 78 % for 4 b and 4 c, respectively). When the reaction was complete, the reaction mixture was cooled to room temperature. The Pd complex coordinated with MeO-WePhos5000 rapidly transferred into the aqueous layer, and the generated diphenylacetylene product was kept in the toluene layer. After a simple phase separation, the aqueous layer was collected and reused in the next reaction. The catalyst recycling process was repeated for 6 times in a same way without clear decrease in GC yields. The final aqueous layer was characterized with inductively coupled plasma-atomic emission spectrometry (ICP-AES) measurement, which confirmed that 98 % Pd was remained in the aqueous phase (Figure S3), highlighting that the catalyst recycling process could be efficiently and easily achieved using the catalyst shuttling approach.
We further investigated the Sonogashira reaction with a variety of (hetero)aryl halides and aromatic alkynes to generate substituted alkynes. In Scheme 3, all electrophiles underwent complete conversions with MeO-WePhos5000 and Pd at 90 °C in 6 h, giving target products with isolated yields of up to 99 %. Electron- deficient, electron-rich and electron- neutral aryl bromides were tolerant in this catalyst system, and could be successfully conducted with ortho-, meta-, and para- substituted (hetero)aryl compounds. Functional groups (i. e., acetyl (9)), and heterocycles (i. e., thiophene (10) and pyridine (12)) could be compatible to generate the corresponding products in good to excellent yields. In addition, the MeO- WePhos5000 4 a could also be employed to promote the Sonogashira cross-coupling with (hetero)aryl chlorides (13, 14).
The vinylation or arylation of alkenes via the Pd- catalyzed reaction was independently discovered by Heck and Mizoroki around 1970,[3b,c] and was widely used in organic synthesis for C C bond formation.[7–8,20] As shown in Scheme 4, MeO- WePhos5000 was investigated in the Pd-catalyzed Heck reac- tions, providing a variety of substituted alkenes under biphasic reaction conditions. Electrophiles of aryl and heteroaryl (i. e., thiophene (18) and pyridine (19, 22)) bromides could be successfully transformed into corresponding products in the presence of acrylates and styrene at high isolated yields with 0.1mol% Pd2(dba)3.
Organometallic reagents of organosilicon and organotin were employed as nucleophiles, respectively, in Hiyama and Stille cross-coupling reactions, delivering biaryl units in pharmaceutical, agrochemical and other areas.[7–8,21] Next, the polymeric ligand 4 a was employed in the Hiyama and Stille reactions as shown in Scheme 5. For both types of cross- couplings, aryl, fused aryl and heteroaryl electrophiles were investigated using either PhSi(OEt)3 or PhSn(Bu)3 as nucleo- philes, providing bi(hetero)aryl products in 86–96 % isolated yields with 0.1 mol% Pd (dba) . For all reactions investigated in this work, the reaction mixtures underwent rapid phase separation at room temperature after reaction, affording products in the organic phase and catalyst kept in the water phase, further facilitating catalyst recycling and separation.
3.Conclusion
In conclusion, we have developed a novel thermoresponsive polymeric ligand, MeO-WePhos, which promoted Pd-cata- lyzed Sonogashira, Heck, Hiyama and Stille reactions under biphasic conditions, facilitating the preparation of correspond- ing alkynes, alkenes or bi(hetero)aryls from a variety of electrophiles and nucleophiles. Importantly, the catalyst shut- tling behavior enabled by the LCST property of PEG has allowed convenient catalyst recycling by simply phase seperation. 98 % Pd was kept in the water phase after recycling the catalsyt solution for 6 times. Given the profound impact of transition-metal-catalyzed covalent bond formation and the increasing demand of sustainable chemistry, this work provides an alternative method to conduct cross-couplings with a shuttling catalyst. We believe that other innovative ligands and new catalytic modes could be developed by introducing the unique property of macromolecules into ligand design.
Acknowledgements
This research was finally supported by the National Natural Science Foundation of China (NSFC, no. 21704016), the start- up funding from Fudan University, and the National Program for Thousand Young Talents of China.
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