A mild and efficient copper-catalyzed N-arylation of unprotected sulfonimidamides using boronic acids

Battula, Satyanarayana; Subbareddy, G. V.; Chakravarthy, I. E.

doi:10.1016/j.tetlet.2013.11.084

Cited by 24 publications

(9 citation statements)

References 25 publications

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“…[11] Since then,o nly af ew synthetic approachesf or the preparation of sulfonimidamides have been reported,u sually involving the nucleophilic substitution of a sulfonimidoyl chloride 7 by an amine (Scheme 1). [12] The required key chloride intermediates 7 have been prepared throughd ifferent strategies that generally hinge on the oxidative imidation of sulfinyl chlorides 5, [11,13] oxidative chlorination of sulfinamides 6 [14] or deoxychlorination of secondary sulfonamides 1. [3,15] However,m ost of these protocols require the use of ap rotecting group, and deprotection to the corresponding unprotected NH sulfonimidamides can be challenging.…”

Section: Introductionmentioning

confidence: 99%

A New, Practical One‐Pot Synthesis of Unprotected Sulfonimidamides by Transfer of Electrophilic NH to Sulfinamides

Izzo

Schäfer

Stockman

et al. 2017

Chemistry A European J

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Unprotected tertiary sulfonimidamides have been prepared in good to excellent yields in a one‐pot transformation from tertiary sulfinamides through NH transfer. The reaction is mediated by commercially available (diacetoxyiodo)benzene and ammonium carbamate in methanol under convenient conditions. A wide range of functional groups are tolerated and initial results indicate that the NH transfer is stereospecific. A small molecule X‐ray analysis of NH sulfonimidamide 2 a and its behavior in selected in vitro assays in comparison to the matched sulfonamide are also reported. This new reaction provides a safe, short and efficient approach to sulfonimidamides, which have been the subject of recent, growing interest in the life sciences.

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Section: Introductionmentioning

confidence: 99%

A New, Practical One‐Pot Synthesis of Unprotected Sulfonimidamides by Transfer of Electrophilic NH to Sulfinamides

Izzo

Schäfer

Stockman

et al. 2017

Chemistry A European J

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“…The boronic‐acid structure‐reactivity relationships observed for thiol and N‐terminal amine coupling reactions (Figure 5) diverges significantly from that typically observed for small‐molecule coupling, in ways that point to significant mechanistic differences. A published report of N−H coupling of boronic acids with sulfonimidamides [44] is typical of small‐molecule methodologies (Figure 6, eqn i): effective coupling is observed with simple arylboronic acids ( A ), while steric bulk in the ortho position results in reduced reaction efficiency ( B ) [45] . Electron‐withdrawing substituents also exhibit lower reaction efficiency, [46] such that an ortho‐nitrophenyl reagent ( C ) gave minimal product.…”

Section: Discussionmentioning

confidence: 98%

Boronic Acid Reagents for Transition‐Metal‐Mediated Cross‐Coupling with Proteins and Peptides

Miller

Ball

2021

Israel Journal of Chemistry

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Transition‐metal catalysis provides new approaches to selectivity and the activation of otherwise inert functional groups. Bioconjugation with protein and peptide substrates presents numerous challenges of functional group activation and selectivity, and transitional‐metal approaches provide important alternative solutions to these challenges. This article describes the development of boronic acid reagents for new selective approaches to modification of peptides and proteins, focusing primarily on catalytic C−X bond formation.

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“…[18a, 26] Limited reports have also used more specific, stable enantioenriched precursors. [27, 10g] Although the N-based reactivity of sulfonimidamides is well documented, [28] there are only a handful of methods that exploit this in asymmetric synthesis. Examples to date use a limited selection of simple sulfonimidamide starting materials and rely on the formation of diastereomeric products, demonstrating that there is no general method for the direct control of configuration at the sulfur centre.…”

Section: Methodsmentioning

confidence: 99%

Exploiting Configurational Lability in Aza‐Sulfur Compounds for the Organocatalytic Enantioselective Synthesis of Sulfonimidamides

et al. 2021

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Methods for establishing the absolute configuration of sulfur-stereogenic aza-sulfur derivatives are scarce, often relying on cumbersome protocols and a limited pool of enantioenriched starting materials. We have addressed this by exploiting, for the first time, a feature of sulfonimidamides in which it is possible for tautomeric structures to also be enantiomeric. Such sulfonimidamides can readily generate prochiral ions, which we have exploited in an enantioselective alkylation process. Selectivity is achieved using a readily prepared bis-quaternized phase-transfer catalyst. The overall process establishes the capability of configurationally labile aza-sulfur species to be used in asymmetric catalysis. Scheme 1. a) Examples of aza-sulfur compounds, including sulfonimidamides. b) Proposed enantioselective synthesis of aza-sulfur compounds by exploiting configurational lability.

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A mild and efficient copper-catalyzed N-arylation of unprotected sulfonimidamides using boronic acids

Cited by 24 publications

References 25 publications

A New, Practical One‐Pot Synthesis of Unprotected Sulfonimidamides by Transfer of Electrophilic NH to Sulfinamides

A New, Practical One‐Pot Synthesis of Unprotected Sulfonimidamides by Transfer of Electrophilic NH to Sulfinamides

Boronic Acid Reagents for Transition‐Metal‐Mediated Cross‐Coupling with Proteins and Peptides

Exploiting Configurational Lability in Aza‐Sulfur Compounds for the Organocatalytic Enantioselective Synthesis of Sulfonimidamides

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