Suzuki-Miyaura coupling reactions using novel metal oxide supported ionic palladium catalysts

Lichtenegger, Georg Johannes; Maier, Manuel C.; Hackl, Markus; Khinast, Johannes G.; Gössler, Walter; Grießer, Thomas; Kumar, Vinit; Gruber‐Wölfler, Heidrun; Deshpande, Parag A.

doi:10.1016/j.molcata.2016.10.033

Cited by 19 publications

(38 citation statements)

References 27 publications

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“…The customized reactor features exchangeable HPLC-columns filled with catalyst particles as well as modules for heating, cooling and mixing. Obtained results [27,29,30] clearly indicate the high potential of the Pd-Ce-Sn-oxides for the synthesis of pharmaceutical and fine chemical intermediates in continuous flow and are promising in terms of the targeted synthesis of valsartan intermediate 13.…”

Section: Electronic Supplementary Materialsmentioning

confidence: 77%

“…For the Suzuki-Miyaura cross-coupling, the use of in-house developed Pd-catalysts with the formula Ce 0.99-x Sn x Pd 0.01 O 2-δ is envisaged. Their applicability for cross-couplings of various orthoand para-substituted bromoarenes with phenylboronic acid has already been reported by our group [27,29]. The heterogeneous catalysts also proved to exhibit high functional group tolerance as well as minimal leaching behavior [27,29].…”

Section: Electronic Supplementary Materialsmentioning

confidence: 79%

“…Their applicability for cross-couplings of various orthoand para-substituted bromoarenes with phenylboronic acid has already been reported by our group [27,29]. The heterogeneous catalysts also proved to exhibit high functional group tolerance as well as minimal leaching behavior [27,29]. Apart from that, the performance of continuous Suzuki crosscoupling reactions was successfully achieved by implementation of the catalysts in an in-house developed packed-bed reactor [30], referred to as Plug & Play reactor.…”

Section: Electronic Supplementary Materialsmentioning

confidence: 88%

“…x Sn x Pd 0.01 O 2-δ [27]. Thirdly, hydrolysis of the methyl ester group is achieved by aqueous base and yields the target compound 13.…”

Section: Electronic Supplementary Materialsmentioning

confidence: 99%

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Multistep synthesis of a valsartan precursor in continuous flow

et al. 2019

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Valsartan is a potent, orally active angiotensin II receptor blocker and is widely used in the treatment of hypertension and chronic heart failure. Herein, we present an approach for the continuous synthesis of a late-stage precursor of valsartan in three steps. The applied synthetic route involves N-acylation, Suzuki-Miyaura cross-coupling and methyl ester hydrolysis. After optimization of the individual steps in batch, they were successfully transferred to continuous flow processes employing different reactor designs. The first step of the synthetic route (N-acylation) as well as the third step (methyl ester hydrolysis) are performed in coil reactor setups. The key step of the reaction cascade (Suzuki-Miyaura cross-coupling) is catalyzed by a heterogeneous palladiumsubstituted cerium-tin-oxide with the molecular formula Ce 0.20 Sn 0.79 Pd 0.01 O 2-δ. The catalyst particles are implemented in an in-house developed packed-bed reactor, which features an HPLC column as fixed-bed. The combination of the individual reaction modules facilitates the consecutive performance of the three reaction steps. Using the developed multistep continuous setup, the targeted valsartan precursor was obtained with up to 96% overall yield.

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Section: Electronic Supplementary Materialsmentioning

confidence: 77%

Section: Electronic Supplementary Materialsmentioning

confidence: 79%

Section: Electronic Supplementary Materialsmentioning

confidence: 88%

“…x Sn x Pd 0.01 O 2-δ [27]. Thirdly, hydrolysis of the methyl ester group is achieved by aqueous base and yields the target compound 13.…”

Section: Electronic Supplementary Materialsmentioning

confidence: 99%

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Multistep synthesis of a valsartan precursor in continuous flow

et al. 2019

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“…For the second step, the Heck coupling of 3 with 2, an inhouse developed heterogeneous Pd-catalyst 45,53 ‡ (Pdsubstituted cerium-tin-oxide with the molecular formula Sn 0.79 Ce 0.20 Pd 0.01 O 2−δ ) was successfully tested for its activity in the novel solvent system. Full conversion of 3 was reached within 30 min (Fig.…”

Section: Heck Coupling In Batchmentioning

confidence: 99%

A chemo-enzymatic tandem reaction in a mixture of deep eutectic solvent and water in continuous flow

et al. 2020

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Development of a Unique Heterogeneous Palladium Catalyst for the Suzuki–Miyaura Reaction using (Hetero)aryl Chlorides and Chemoselective Hydrogenation

et al. 2017

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A unique heterogeneous palladium catalyst (7% Pd/WA30) supported on an anion exchange resin, which contains N,N‐dimethylaminoalkyl functionalities on the polymer backbone, was developed. 7% Pd/WA30 could smoothly catalyze Suzuki–Miyaura reactions of even less reactive heteroaryl chlorides and heteroarylboronic acids to afford various (hetero)biaryls due to the electron‐donating effect of the tert‐amines on WA30 to Pd species. It was also applicable as a chemoselective hydrogenation catalyst, showing inactivity for the hydrogenolysis of tert‐butyldimethylsilyl (TBS) ethers, alkyl benzyl ethers, and benzyl alcohols. The tert‐amines on WA30 acted as moderate catalyst poisons for Pd, resulting in chemoselective hydrogenation. 7% Pd/WA30 was reused for at least five times without any loss of the hydrogenation catalytic activity.magnified image

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Suzuki-Miyaura coupling reactions using novel metal oxide supported ionic palladium catalysts

Cited by 19 publications

References 27 publications

Multistep synthesis of a valsartan precursor in continuous flow

Multistep synthesis of a valsartan precursor in continuous flow

A chemo-enzymatic tandem reaction in a mixture of deep eutectic solvent and water in continuous flow

Development of a Unique Heterogeneous Palladium Catalyst for the Suzuki–Miyaura Reaction using (Hetero)aryl Chlorides and Chemoselective Hydrogenation

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