An efficient and green La(OTf)3 catalyzed Petasis borono–Mannich reaction for the synthesis of tertiary amines

Reddy, Bijivemula N.; Chinthaparthi, Radha Rani; Reddy, S. M.; Pathak, Madhvesh

doi:10.1007/s11164-016-2551-6

Cited by 11 publications

(5 citation statements)

References 29 publications

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“…Another series of similar diphenylmethanamines, generally containing a morpholino instead of a pyrrolidino alkyl moiety, was synthesized using a catalysis based on chitosan or trititanate nanotubes in high yield. The methodology could also be extended to a series of piperazine-substituted aminophenols. , Other catalysts, including lanthanum(III) trifluoromethanesulfonate, Mg–Al mixed oxides, and 4 Å supported copper catalysts, were also applied in the PR of salicylaldehyde, morpholine, and arylboronic acid. , 2-(Aryl(piperidin-1-yl)methyl)phenols sharing the same or higher structural familiarity as 28 were recently used as substrates for the synthesis of 9-aryl-2,3,4,9-tetrahydro-1 H -xanthen-1-ones in a FeCl 3 -mediated approach involving nucleophilic substitution and intramolecular cyclization steps . A microwave-assisted PR catalyzed by CuO-nanoparticle-decorated reduced graphene oxide composite was recently reported for the synthesis of similar aminophenols .…”

Section: Three-component Petasis Reactionsmentioning

confidence: 99%

Reactivity and Synthetic Applications of Multicomponent Petasis Reactions

2019

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The Petasis boron–Mannich reaction, simply referred to as the Petasis reaction, is a powerful multicomponent coupling reaction of a boronic acid, an amine, and a carbonyl derivative. Highly functionalized amines with multiple stereogenic centers can be efficiently accessed via the Petasis reaction with high levels of both diastereoselectivity and enantioselectivity. By drawing attention to examples reported in the past 8 years, this Review demonstrates the breadth of the reactivity and synthetic applications of Petasis reactions in several frontiers: the expansion of the substrate scope in the classic three-component process; nonclassic Petasis reactions with additional components; Petasis-type reactions with noncanonical substrates, mechanism, and products; new asymmetric versions assisted by chiral catalysts; combinations with a secondary or tertiary transformation in a cascade- or sequence-specific manner to access structurally complex, natural-product-like heterocycles; and the synthesis of polyhydroxy alkaloids and biologically interesting molecules.

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Section: Three-component Petasis Reactionsmentioning

confidence: 99%

Reactivity and Synthetic Applications of Multicomponent Petasis Reactions

2019

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“…Thus, recently Yuan and co‐workers showed how this reaction could be highly enhanced by sonication. Higher yields were not connected to all the tested substrates, but this method represents a valid alternative to the previously reported ones, that need longer reaction times with the same poor yields yet in the presence of catalysts such as TFA, La(OTf) 3 , molecular sieves or other energy sources, like MW (Scheme ) …”

Section: Multi‐component Reactions (Mcrs)mentioning

confidence: 87%

Ultrasound‐Assisted Multicomponent Reactions, Organometallic and Organochalcogen Chemistry

et al. 2018

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In the last two decades, the search for sustainability in chemical reactions has attached a lot of attention. In this focus review, the use of ultrasound (US) as an alternative energy source in organic synthesis is presented. The improvement of the performance of chemical reactions due to the cavitation effect has been previously studied and described. The use of US guarantees often higher yields than other green methodologies, as microwave or ball milling. The impressive positive effect of US in organic synthesis are demonstrated in this review mainly in organometallic and multi-component reactions (MCRs), aimed to prepare bioactive compounds. A particular attention is dedicated to the US-assisted synthesis of valuable organochalcogen compounds with pharmacological activity.[a] F.

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Section: Acid-catalyzed Petasis Reactionmentioning

confidence: 99%

“…The highest yield (98%) of tertiary amine 27 was recorded when aldehyde 5 was treated with morpholine 14 and (2-chlorophenyl)boronic acid 26 under microwave irradiation using La(OTf)3 catalyst (Scheme 7). However, by using benzaldehydes (instead of salicylaldehydes) under the same reaction conditions, moderate yields of the corresponding products were observed (two examples, 75% and 78% yields) [39]. Vinylglycines or β,γ-unsaturated α-amino acids represent a unique class of optically pure nonproteinogenic amino acids, which display antimicrobial activity and act as synthetic intermediates in various organic transformations [40].…”

Section: Acid-catalyzed Petasis Reactionmentioning

confidence: 99%

Recent Trends in the Petasis Reaction: A Review of Novel Catalytic Synthetic Approaches with Applications of the Petasis Reaction

Saeed,

Munawar,

Ahmad

et al. 2023

Molecules

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The Petasis reaction, also called the Petasis Borono–Mannich reaction, is a multicomponent reaction that couples a carbonyl derivative, an amine and boronic acids to yield substituted amines. The reaction proceeds efficiently in the presence or absence of a specific catalyst and solvent. By employing this reaction, a diverse range of chiral derivatives can easily be obtained, including α-amino acids. A broad substrate scope, high yields, distinct functional group tolerance and the availability of diverse catalytic systems constitute key features of this reaction. In this review article, attention has been drawn toward the recently reported methodologies for executing the Petasis reaction to produce structurally simple to complex aryl/allyl amino scaffolds.

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An efficient and green La(OTf)3 catalyzed Petasis borono–Mannich reaction for the synthesis of tertiary amines

Cited by 11 publications

References 29 publications

Reactivity and Synthetic Applications of Multicomponent Petasis Reactions

Reactivity and Synthetic Applications of Multicomponent Petasis Reactions

Ultrasound‐Assisted Multicomponent Reactions, Organometallic and Organochalcogen Chemistry

Recent Trends in the Petasis Reaction: A Review of Novel Catalytic Synthetic Approaches with Applications of the Petasis Reaction

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