Aryl/heteroaryl pentafluorobenzenesulfonates (ArOPFBs): new electrophilic coupling partners for room temperature Suzuki–Miyaura cross-coupling reactions

Joseph, Jayan T.; Sajith, Ayyiliath M.; Ningegowda, Revanna C.; Nagaraj, Archana; Rangappa, K. S.; Shashikanth, S.

doi:10.1016/j.tetlet.2015.07.033

Cited by 24 publications

(9 citation statements)

References 49 publications

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“…In 2015, Shashikanth and co-workers reported the high yielding Suzuki-Miyaura coupling of isoxazol-4-ylboronic acid (40) with aryl pentafluorobenzenesulfonates (ArOPFB) under mild conditions (r.t.) (Scheme 18). 33 The desired product 50 was obtained in an excellent yield (90%).…”

Section: Scheme 17 C-c Bond Formation At the 4-position Of Isoxazole mentioning

confidence: 96%

“…A number of Suzuki-Miyaura coupling reactions at the 4-position of isoxazoles have been reported. [29][30][31][32][33] In 2007, Sherman and co-workers reported the Suzuki-Miyaura coupling of base-labile isoxazolylboron species 47 in the synthesis of 48 (Scheme 16). 29a However, neither detailed experimental procedure nor an exact yield were reported in their manuscript.…”

Section: Short Review Syn Thesismentioning

confidence: 99%

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Step-by-Step Multifunctionalization of Isoxazoles Based On SEAr Reactions and C–H Direct Arylations

2017

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Functionalized isoxazoles are important as pharmaceuticals and agrochemicals. Generally, electrophilic aromatic substitution or generation of carbanions/electrophilic trapping approach is used to introduce functional groups into unsubstituted heteroaromatics. However, these approaches have not been simple to apply to unsubstituted isoxazoles due to their poor nucleophilicity and instability under basic conditions. Recently several approaches have been reported to overcome these problems. This review summarizes the functionalization of isoxazoles, including SEAr reactions and C–H direct arylations, towards the step-by-step multifunctionalization of isoxazoles.1 Introduction2 SEAr Reaction of Isoxazoles3 Preparation of Isoxazolyl Anions and Their Use for the Synthesis of Functionalized Isoxazoles4 Other C–C and C–N Bond Formations of Isoxazoles5 Transition-Metal-Catalyzed C–H Direct Functionalization of Isoxazoles6 Step-by-Step Multifunctionalization of Isoxazoles7 Summary and Outlook

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Section: Scheme 17 C-c Bond Formation At the 4-position Of Isoxazole mentioning

confidence: 96%

Section: Short Review Syn Thesismentioning

confidence: 99%

Step-by-Step Multifunctionalization of Isoxazoles Based On SEAr Reactions and C–H Direct Arylations

2017

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“…In general, methylation occurs on an activated substrate such as C‐halides (Cl, Br), C‐OTf, C‐OSO 2 C 6 F 5 , and halogenated acrylates . In many cases, methylation is carried out on late‐stage intermediates, and more interestingly, owing to the excellent functional group tolerance, TMB‐mediated methylation chemistry is often published in journals relevant to medicinal chemistry, in which functional groups, such as secondary amine, oxetane, acetal, aldehyde, ketone, imidazole, aniline, thiol ether, indole, ester, and amide are often designed into pharmaceutical molecules or their corresponding intermediates.…”

Section: Methylation By Using Conventional Reagentsmentioning

confidence: 99%

Recent Advances in Methylation: A Guide for Selecting Methylation Reagents

Chen

2018

Chemistry A European J

189

121

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Methylation is a well‐known structural modification in organic and medicinal chemistry. This review summarizes recent advances in methylation by categorizing specific methylation reagents. The challenges of mono N‐methylation of aliphatic amines and N‐methylation of peptides are discussed. This review will be useful for chemists wanting to select the appropriate reagents for methylation chemistry. Based on the large diversity of methylation reagents and their wide scope, this review also broadens perspectives on which strategies to select for utilizing a particular methylation, resulting in an increased flexibility in synthetic route planning.

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“…The use of highly demanding catalytic systems has enabled the cross‐coupling of even electron‐rich (hetero) aryl chlorides and pseudohalides (Tosylates, mesylates) . In our successful trials, we have demonstrated a versatile electrophilic counterpart (ArOPFBs) which allows the cross‐coupling process to be performed under extremely milder conditions . Despite these advances, the use of hetero halide containing a free ‐NH as one of the coupling partner still remains a challenge.…”

Section: Introductionmentioning

confidence: 99%

Suzuki‐Miyaura cross–coupling reaction in water: facile synthesis of (hetero) aryl uracil bases using potassiumorganotrifluoroborates under microwave irradiation.

et al. 2016

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In this paper, we report the use of (hetero) aryl potassiumorganotrifluoroborate salts as versatile nucleophilic organoboron reagents in the Suzuki‐Miyaura cross‐coupling reaction of an electron rich 6‐chloro 3‐methyl uracil in water under microwave irradiation. A comparative study of the cross‐coupling reaction of this chloro uracil analogue with different nucleophilic organoboron source revealed the superior reactivity of (hetero) aryl potassiumorganotrifluoroborates in water under microwave irradiation. Diversely functionalised (hetero) aryl uracil bases, which are known possess a wide range of applications in chemical biology, were efficiently synthesized using this optimised protocol.

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Aryl/heteroaryl pentafluorobenzenesulfonates (ArOPFBs): new electrophilic coupling partners for room temperature Suzuki–Miyaura cross-coupling reactions

Cited by 24 publications

References 49 publications

Step-by-Step Multifunctionalization of Isoxazoles Based On SEAr Reactions and C–H Direct Arylations

Step-by-Step Multifunctionalization of Isoxazoles Based On SEAr Reactions and C–H Direct Arylations

Recent Advances in Methylation: A Guide for Selecting Methylation Reagents

Suzuki‐Miyaura cross–coupling reaction in water: facile synthesis of (hetero) aryl uracil bases using potassiumorganotrifluoroborates under microwave irradiation.

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