Metal‐Free Efficient, General and Facile Iododecarboxylation Method with Biodegradable Co‐Products

Kulbitski, Kseniya; Nisnevich, G. A.; Gandelman, Mark

doi:10.1002/adsc.201100145

Cited by 78 publications

(56 citation statements)

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“…However, the development of their chemistry has been an uneven process, most likely, due to the lack of selective, practical and high yielding methods of their synthesis 10. Recently, we reported a robust, general and efficient method for synthesis of alkyl iodides from carboxylic acids through their simple treatment with commercially available 1,3-diiodo-5,5-dimethylhydantoin (DIH) under visible light (VIS) irradiation 11. We now report that, contrary to other iododecarboxylation approaches,10 d our method can be uniquely extended to α-chloroalkanoic acids.…”

Section: Resultsmentioning

confidence: 99%

Enantioselective assembly of tertiary stereocenters via multicomponent chemoselective cross-coupling of geminal chloro(iodo)alkanes

et al. 2016

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Section: Resultsmentioning

confidence: 99%

Enantioselective assembly of tertiary stereocenters via multicomponent chemoselective cross-coupling of geminal chloro(iodo)alkanes

et al. 2016

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“…4‐1). Selectfluor,– dibromoisocyanuric acid, t BuOCl, DIH, NIS and I 2 were employed for the synthesis of mono‐, di‐ and trifluoromethyl arenes, bromo‐, chloro‐ and iodo‐ methyl arenes. Decarboxylative trifluoromethylation, trifluoromethylthiolation cyanation and acetoxylation, were independently developed (Scheme ).…”

Section: Decarboxylationmentioning

confidence: 99%

Arylacetic Acids in Organic Synthesis

et al. 2019

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Arylacetic acids are widely used in organic reactions and their recent advances are summarized in six categories according to their triggered pathways: (1) the acid as directing group in ortho-or meta-CÀ H activation; (2) decarboxylation; (3) deprotonation; (4) nucleophilic methylenes; (5) nucleophilic acids; (6) electrophilic acids. Reactions with alkenes, alkynes, aldehydes, amines, water, Grignard reagents, silanes and so forth are discussed. We hope this Minireview will promote future research in this area. Recently, the Zeng group [3g] reported a weakly coordinationassisted alkynylation of arylacetic acids with iridium catalysis under air atmosphere (Eq. 2-2). It was supported the sixmembered ring cycloiridiated 2.5 acted as the key intermediate. The alkynylation of indole, thiophene, pyrrole, and benzo[b] thiophene afforded better yields than phenylacetic acids. The acid moiety could also participated in the intramolecular ortho-CÀ H activation, which was developed by the Shi group to obtain lactonization 2.6 (Eq. 2-3) (Scheme 2). Meta-CÀ H ArylationThe study of Yu group [3e] in 2017 revealed a successful control of meta selectivity 3.1 of arylation from aryl iodides (Eq. 3-1). The use of mono-protected 3-amino-2-hydroxypyridine (as ligand) and 2-carbomethoxynorbornene (NBE-CO 2 Me) were crucial. In the absence of NBE-CO 2 Me, only ortho-arylated product was obtained. This method was still efficient in a gramsale (Scheme 3). Decarboxylation Decarboxylative CouplingAs shown in Scheme 4, the decarboxylation could generate benzyl radicals 4.1. Then, direct couplings of 4.1 with diverse [ + ] These authors contributed equally. Scheme 1. Six categories based on triggered mechanism. 2 3 4 5 6 7 8 . Passerini Three-Component ReactionThe Passerini reaction was the oldest multicomponent reaction (MCR) [37d] in which isocyanides, carboxylic acids and aldehydes were used. It was powerful for the rapid construction of complex molecules. The tactic to expand the scope of Passerini reaction was to use surrogates of the carbonyl partners. As described in Scheme 51, syn-chlorooximes, [37b] diazoketones, [37c] alcohols, [37d,e] azirines [37f] and isatins [37g] could be employed instead of aryl or alkyl aldehydes [37a] (Scheme 51). Besides, in 2018, Zhang and co-workers [37] have firstly reported asymmetric phosphoric acid-catalyzed four-component Ugi reaction, which Scheme 45. BTM-catalyzed cycloaddition. Scheme 46. HBTM-catalyzed cycloaddition. Scheme 47. TFA-catalyzed reaction. Scheme 48. Friedel-Crafts triggered tandem reactions. Scheme 49. C-acylation of 1,3-diones. Scheme 50. C-acylation of 1,3-indandiones.

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“…[7] Furthermore, their unique chemical and structural properties create further curiosity. [8] However, methodologies available for the construction of benzodioxin skeletons [9][10][11][12][13][14][15][16] are documented below (Scheme 3).…”

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confidence: 99%

Revisiting the Addition of in‐situ Nucleophiles to Allenic Ketones: An Entry Towards Synthesis of Benzodioxins

Sahoo

Sarkar

2020

Eur J Org Chem

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The manuscript delineates a revisit towards regioselective addition of in situ generated negative nucleophiles to allenic ketones in the presence of a base. A wide variety of allenic ketones as well as nucleophiles are viable in this transformation. A direct ring annulation towards the challenging benzodioxin skeleton synthesis has been developed. Environmentally benign protocol and wide substrate scope are the notable features of this methodology.

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Metal‐Free Efficient, General and Facile Iododecarboxylation Method with Biodegradable Co‐Products

Cited by 78 publications

References 18 publications

Enantioselective assembly of tertiary stereocenters via multicomponent chemoselective cross-coupling of geminal chloro(iodo)alkanes

Enantioselective assembly of tertiary stereocenters via multicomponent chemoselective cross-coupling of geminal chloro(iodo)alkanes

Arylacetic Acids in Organic Synthesis

Revisiting the Addition of in‐situ Nucleophiles to Allenic Ketones: An Entry Towards Synthesis of Benzodioxins

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