Recent Advances on Diverse Decarboxylative Reactions of Amino Acids. Issue 10 (13th February 2019)

• Record Type: Journal Article
• Authors: Rahman, Matiur; Mukherjee, Anindita; Kovalev, Igor S.; Kopchuk, Dmitry S.; Zyryanov, Grigory V.; Tsurkan, Mikhail V.; Majee, Adinath; Ranu, Brindaban C.; Charushin, Valery N.; Chupakhin, Oleg N.; Santra, Sougata
• Is Part Of: Advanced synthesis & catalysis. Volume 361:Issue 10(2019)
• Page Start: 2161
• Page End: 2214
• Publication Date: 2019-02-13
• Subjects: amino acids -- azomethine ylides pathway -- decarboxylation -- photoredox catalysis -- radical pathway; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201801331
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: This review aims to report recent advances on decarboxylative reactions of amino acids catalyzed by transition metals or non‐metals and the growing opportunities they present in the construction of complex chemical scaffolds for applications encompassing natural product synthesis, synthetic methodology development, and functional materials. Different decarboxylative reactions have been highlighted such as radical, photoredox and metal and metal‐free coupling reactions. etc. The review is divided into two main sections: one deals with reactions via radical pathways and the other via azomethine ylide pathways. The reactions have been discussed in more detail with particular emphasis on their useful applications and mechanistic illustrations. Abbreviations : 1, 3‐DCB: 1, 3‐dicyanobenzene; 1, 4‐DCB: 1, 4‐dicyanobenzene; Acr: acridinium; BI: benziodoxolone; Boc: tert ‐butoxycarbonyl; CB: conduction band; CBX: cyanobenziodoxolone; CFL: compact fluorescent lamp; DBU: 1, 8‐diazabicyclo[5.4.0]undec‐7‐ene; DCA: 9, 10‐dicyanoanthracene; DCB: 1, 2‐dichlorobenzene; DCE: 1, 2‐dichloroethane; DDDS: bis(4‐chlorophenyl) disulfide; DIPEA: diisopropylethylamine; DMA: N, N ‐dimethylacetamide; DMF: N, N ‐dimethylformamide; DMSO: dimethyl sulfoxide; DNA: deoxyribonucleic acid; dtbbpy: 4, 4′‐di‐ tert ‐butyl‐2, 2'‐bipyridine; DTBP: di‐ tert ‐butyl peroxide; equiv.: equivalent; ET: electron transfer; h: hour; HE: Hantzsch ester; LED: light‐emitting diode; min: minutes; mL: millilitre; MS: molecular sieves; MW: microwave; nm: nanometer; NS: nanosphere; Nu: nucleophile; ODCB: o ‐dichlorobenzene; PA‐1: (±)‐1, 1′‐binaphthyl‐2, 2′‐diyl hydrogen phosphate; PC: photocatalyst; PET: photoinduced electron transfer; PEG: polyethylene glycol; PG: protecting group; Phen: phenanthrene; PTA: phosphotungstic acid 44‐hydrate; RNA: ribonucleic acid; r.t.: room temperature; SET: single‐electron transfer; TBAI: tetrabutylammonium iodide; TBHP: tert ‐butyl hydroperoxide; TFA: trifluoroacetic acid; THF: tetrahydrofuran; TMEDA: N, N, N′, N′ ‐tetramethylethylenediamine; TS: transition state; UV: ultraviolet; VB: valence band; W: watt. Abstract :