Design and Reactivity of Organic Functional Groups — 2-Pyridylsulfonates as Nucleofugal Esters: Remarkably Mild Transformations into HAlides and Olefins

Hannessian, S.; Kagotani, M.; Komaglou, K.

doi:10.3987/com-88-s134

Cited by 34 publications

(20 citation statements)

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“…Similarly, the pyridylsulfonyl group was described as a versatile protecting group 14. Pyridylsulfonyl chloride is, however, still not commercially available and its preparation is not straightforward 15. Other sulfonyl protecting groups that have also been reported are the (β‐trimethylsilyl)ethanesulfonyl (SES)16,17 and the 2‐(1,3‐dioxan‐2‐yl)ethylsulfonyl (Dios)18 or heteroarenesulfonyl groups;19,20 they are, however, not commercially available.…”

Section: Introductionmentioning

confidence: 99%

Mild Electrochemical Deprotection of N‐Phenylsulfonyl N‐Substituted Amines Derived from (R)‐Phenylglycinol

et al. 2007

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The electrochemical reduction of N‐phenylsulfonyl N‐substituted amines in a protic medium under constant cathodic potential was found to be a mild desulfonylation method, which is able to challenge the chemical ones. The influence of the nature of the N‐substituents was considered in order to clarify the mechanistic aspects and to evaluate the scope of the method.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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Section: Introductionmentioning

confidence: 99%

Mild Electrochemical Deprotection of N‐Phenylsulfonyl N‐Substituted Amines Derived from (R)‐Phenylglycinol

et al. 2007

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“…[10] To our knowledge, the quisylate group has only been used twice as a leaving group, in E1-type pyrolysis reactions [11] and in nucleophilic bromination reactions leading to inversion of configuration. [12] Menthyl quisylate 4 reacted with TiBr 4 to give menthyl bromide product at over ten times the rate of naphthyl sulfonate 3 ( Table 1, entries 3 and 4). The quisylate leaving group in substrate 4 also out-performed leaving groups in 5 and 6 each containing multiple ether oxygen atoms.…”

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confidence: 99%

Stereoretentive Halogenations and Azidations with Titanium(IV) Enabled by Chelating Leaving Groups

Lepore

Mondal

et al. 2008

Angew Chem Int Ed

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Titanium does it again! With the help of nucleophile‐assisting leaving groups (NALGs), alkyl bromides, iodides, and, for the first time, azides are obtained from sulfonates with complete retention of configuration. Critical to the design of these new titanium(IV) reactions has been the use of NALGs which are thought to chelate the Lewis acid reagent in the transition state promoting an SNi‐type mechanism.

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“…This result was surprising, and it appears that the presence of the alkyl tosylate among the other components in the reaction mixture plays a role in determining the distribution of products. In an effort to explore a possible coordination with the catalyst, 34 we tried the cross-coupling reaction of 1a with the (2-pyridyl) and (3-pyridyl) sulfonate esters 2c and 2d of N -Boc 3-hydroxypiperidine. Unfortunately, the amount of biaryl 4 was increased (∼30%) at the expense of the desired cross-coupling product 5 (19 and 12%, respectively) ( Scheme 2 , Table 1, entries 6 and 7).…”

Section: Resultsmentioning

confidence: 99%

Ni-Catalyzed Reductive and Merged Photocatalytic Cross-Coupling Reactions toward sp³/sp²-Functionalized Isoquinolones: Creating Diversity at C-6 and C-7 to Address Bioactive Analogues

et al. 2020

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Naturally occurring isoquinolones have gained considerable attention over the years for their bioactive properties. While the late-stage introduction of various functionalities at certain positions, namely, C-3, C-4, and C-8, has been widely documented, the straightforward introduction of challenging sp 3 carbon-linked acyclic aminoalkyl or aza- and oxacyclic appendages at C-6 and C-7 remains largely underexplored. Interest in 6-substituted azacyclic analogues has recently garnered attention in connection with derivatives exhibiting anticancer activity. Reported here is the first application of the versatile and recently emerging field of Ni-catalyzed reductive cross-coupling reactions to the synthesis of 6- and 7- hetero(cyclo)alkyl-substituted isoquinolones. In a second and complementary approach, a new set of C-6- and C-7-substituted positional isomers of hetero(cyclo)alkyl appendages were obtained from the merging of photocatalytic and Ni-catalyzed coupling reactions. In both cases, 6- and 7-bromo isoquinolones served as dual-purpose reacting partners with readily available tosylates and carboxylic acids, respectively.

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Design and Reactivity of Organic Functional Groups — 2-Pyridylsulfonates as Nucleofugal Esters: Remarkably Mild Transformations into HAlides and Olefins

Cited by 34 publications

References 0 publications

Mild Electrochemical Deprotection of N‐Phenylsulfonyl N‐Substituted Amines Derived from (R)‐Phenylglycinol

Mild Electrochemical Deprotection of N‐Phenylsulfonyl N‐Substituted Amines Derived from (R)‐Phenylglycinol

Stereoretentive Halogenations and Azidations with Titanium(IV) Enabled by Chelating Leaving Groups

Ni-Catalyzed Reductive and Merged Photocatalytic Cross-Coupling Reactions toward sp³/sp²-Functionalized Isoquinolones: Creating Diversity at C-6 and C-7 to Address Bioactive Analogues

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Design and Reactivity of Organic Functional Groups — 2-Pyridylsulfonates as Nucleofugal Esters: Remarkably Mild Transformations into HAlides and Olefins

Cited by 34 publications

References 0 publications

Mild Electrochemical Deprotection of N‐Phenylsulfonyl N‐Substituted Amines Derived from (R)‐Phenylglycinol

Mild Electrochemical Deprotection of N‐Phenylsulfonyl N‐Substituted Amines Derived from (R)‐Phenylglycinol

Stereoretentive Halogenations and Azidations with Titanium(IV) Enabled by Chelating Leaving Groups

Ni-Catalyzed Reductive and Merged Photocatalytic Cross-Coupling Reactions toward sp3/sp2-Functionalized Isoquinolones: Creating Diversity at C-6 and C-7 to Address Bioactive Analogues

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Ni-Catalyzed Reductive and Merged Photocatalytic Cross-Coupling Reactions toward sp³/sp²-Functionalized Isoquinolones: Creating Diversity at C-6 and C-7 to Address Bioactive Analogues