15. The pyrrolo[2,1-a]isoquinoline core structure is prevalent in marine natural products and its fluorinated derivatives are potential medicinal compounds. Herein is described a tungsten-catalysed decarboxylative [3 + 2] cycloaddition aromatization process that could be used to construct trifluoromethyl-pyrrolo[2,1-a]isoquinolines. This photocatalytic reaction tolerates a panel of functional groups including ester, nitrile, ketone and alkene (24 examples, up to 94% yield). The […]
14. The photo-induced cleavage of C(sp2)–Cl bonds is an appealing synthetic tool in organic synthesis, but usually requires the use of high UV light, photocatalysts and/or photosensitizers. Herein is described a direct photo-induced chloroarene activation with UVA/blue LEDs that can be used in the reductive Heck cyclization of indoles and without the use of a photocatalyst or photosensitizer. The […]
13. Herein, we describe a soluble iron(II)-phthalocyanine, [FeII(tBu4Pc)(py)2] (Pc = phthalocyaninato(2–)), as an effective catalyst in intramolecular C(sp3)–H bond amination, with alkyl azides as the nitrogen source, to afford the amination products in moderate to excellent yields with a broad substrate scope. Chem. Commun., 2021, 57, 10711–10714. DOI: 10.1039/d1cc04573c.
12. A series of platinum(II) complexes supported by terphenyl diacetylide as well as diimine or bis-N-heterocyclic carbene (NHC) ligands have been prepared. The diacetylide ligands adopt a cis coordination mode featuring non-planar terphenyl moieties as revealed by X-ray crystallographic analyses. The electrochemical, photophysical and photochemical properties of these platinum(II) complexes have been investigated. These platinum(II) diimine complexes show broad emission with peak maxima […]
11. Metal-catalyzed C@N bond formation reactions via acylnitrene transfer have recently attracted much attention, but direct detection of the proposed acylnitrenoid/acylimido M-(NCOR) (R=aryl or alkyl) species in these reactions poses a formidable challenge. Herein, we report on Ru(NCOR) intermediates in C@N bond formation catalyzed by [RuIV-(Por)Cl2]/N3COR, a catalytic method applicable to aziridine/ oxazoline formation from alkenes, amination of substituted indoles, a-amino […]
10. In the presence of luminescent [Pt(O^N^C^N)] complexes under visible light (410 nm) irradiation, aryl radicals derived from reductive aryl–chloride/bromide bond cleavage were trapped by aryl alkenes and afforded a series of anti-Markonikov hydroarylated compounds. Besides, a protocol for [Pt(O^N^C^N)]-catalyzed intramolecular photocyclization of acrylanilides to give structurally diverse 3,4-dihydroquinolinones has been developed. (Angew. Chem. Int. Ed. […]
9. A panel of natural aliphatic tertiary alkaloids (R3N) were directly converted to R3N+–NH− (without the need to prepare protected aminimides R3N+–NR′− followed by deprotection) by [Mn(TDCPP)Cl]-catalysed N-amination reaction, with O-(2,4-dinitrophenyl)hydroxylamine as the nitrogen source, in up to 98% yields under mild reaction conditions. （Chemical Communications 2020, 56, 9102–9105. DOI: 10.1039/D0CC02934C）
8. A series of bis(tridentate) cyclometalated oligopyridine complexes [FeII(C∧N∧N)(L)]+ have been synthesized via the reactions of [FeII(C∧Npy∧Npy)Br(PMe3)2] (1, HC∧Npy∧Npy = 6- (phenyl)-2,2′-bipyridine) and [FeII(C∧Nppy∧Nisoquin)Br(PMe3)2] (2, HC∧Nppy∧Nisoquin = 3-(4,6-diphenylpyridin-2-yl)isoquinoline) with tridentate ligands L, affording [FeII(C∧Npy∧Npy)(4′-R-tpy)]+ (3a−e, R = H, Cl, p-ClC6H4, p-MeOC6H4, p-tol, respectively; tpy = 2,2′:6′,2″-terpyridine), [FeII(C∧Nppy∧Nisoquin)(tpy)]+ (4), [FeII(C∧Npy∧Npy)(6-(Ph2PCH2)-bpy)]+ (5, bpy = 2,2′-bipyridine), and [FeII(C∧Npy∧Npy)(6-NHC-bpy)]+ […]
7. Direct C–H bond functionalization catalyzed by non-precious transition metals is an attractive strategy in synthetic chemistry. Compared with the precious metals rhodium, palladium, ruthenium, and iridium commonly used in this field, catalysis based on non-precious metals, especially the earth-abundant ones, is appealing due to the increasing demand for environmentally benign and sustainable chemical processes. […]
6. The realization of photocatalysis for practical synthetic application hinges on the development of inexpensive photocatalysts which can be prepared on a large scale. Herein an air-stable, visible-light-absorbing photoluminescent tungsten(VI) complex which can be conveniently prepared at the gram-scale is described. This complex could catalyse photochemical organic transformation reactions including borylation of aryl halides, such […]
5. Ruthenium porphyrin catalysed direct intermolecular amino-oxyarylation of alkenes including styrenes and 1,3-dienes to give primary amines with O-(2,4-dinitrophenyl)hydroxylamine as the amine source was achieved in moderate to good yields under mild reaction conditions. Spectroscopic analyses revealed that a ruthenium nitrido complex was the key reaction intermediate for the amino-oxyarylation reaction.(Chem. Commun. 2020, 56, 137-140; DOI: 10.1039/C9CC08043K) […]
4. Transition-metal-catalyzed direct C–H bond amination is an attractive strategy in preparation of nitrogen containing molecules which are common in naturally occurring and pharmaceutically important compounds. Comparing to the precious metals commonly used in this reaction, non-precious metals such as iron are abundant in earth, relatively low toxic, and more biocompatible, which meet the increasing […]
3. Ruthenium(II) complexes bearing a tridentate bis(N-heterocyclic carbene) ligand reacted with iminoiodanes (PhI=NR) resulting in the formation of isolable ruthenium(III)–amido intermediates, which underwent cleavage of a C@N bond of the tridentate ligand and formation of an N-substituted imine group. The RuIII–amido intermediates have been characterized by 1H NMR, UV/Vis, ESIMS, and X-ray crystallography. DFT calculations […]
2. Although photoredox catalysis employing Ru(II) and Ir(III) complexes as photocatalysts has emerged as a versatile tool for oxidative C–H functionalization under mild conditions, the need for additional reagents acting as electron donor/scavenger for completing the catalytic cycle undermines the practicability of this approach. Herein we demonstrate that photo-induced oxidative C–H functionalization can be catalysed […]
1. The platinum(II) photo-catalyzed difluoroalkylation of cinnamic acids and alkynes for selective construction of E-,Z-difluoroalkyl alkenes and difluoroalkyl alkenyl iodides, respectively, were achieved under mild conditions. The high efficiency, good substrate scope and high selectivity altogether highlight the prospect of Pt(II) photocatalysts in visible-light-driven organic transformation reactions.(Chem. Commun. 2017, 53, 8948-8951; DOI: 10.1039/C7CC03823B) […]
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