Orthogonal synthesis of pyrroles and 1,2,3-triazoles from vinyl azides and 1,3-dicarbonyl compounds

Ng, Eileen Pei Jian; Wang, Yi‐Feng; Hui, Benjamin Wei-Qiang; Lapointe, Guillaume; Chiba, Shunsuke

doi:10.1016/j.tet.2011.08.006

Cited by 76 publications

(27 citation statements)

References 67 publications

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“…In(III) Dibromocations as π-Lewis Acids The airstable N,N ′ -bis- (2,6- to quantitatively produce PLA with controlled molecular weights and polydispersity indexes (PDIs) ranging from 1.3 to 1.6 (67). 94 The In(III) complex polymerizes preferentially the L-LA enantiomer with a constant rate five time superior to that of D-LA enantiomer, which allows the formation of stereoblock isotactic polymers of the type PLLA-b-PDLA.…”

Section: N-heterocyclic Carbene (Nhc) Ligandsmentioning

confidence: 99%

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Gallium and Indium Compounds in Homogeneous Catalysis

Dagorne

Fliedel

Frémont

2016

Encyclopedia of Inorganic and Bioinorganic Chemistry

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The present contribution highlights the most recent and representative developments on the use of Ga and In species in homogeneous catalysis. Recent studies of various ligand‐supported Ga(III) and In(III) compounds in cyclic esters polymerization catalysis for the production of biodegradable polyester materials are also included. Various organic transformations may now be catalyzed using Ga(III) and In(III) Lewis acids allowing access to a wide range of valuable organic molecules through diverse reaction sequences. The recent use of stable and robust N ‐heterocyclic carbene Ga(III) and In(III) compounds as strong π‐Lewis acid catalysts for various organic reactions is also discussed: such species are certainly promising for the future developments of Ga(III)‐ and In(III)‐mediated reactions. Although Lewis acid‐assisted reactions certainly dominate the field in Ga(III) and In(III) chemistry, discrete low‐valent In(I) species, presently emerging in catalysis, clearly display a distinct reactivity allowing their exploitation both as soft Lewis acids and alkyl‐/allyl‐/arylating agents.

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Section: N-heterocyclic Carbene (Nhc) Ligandsmentioning

confidence: 99%

“…The role of indium is likely to promote the formation of a more nucleophilic indium-enolate intermediate from diketone tautomerization 67. Surveying other Lewis acids based on Zn(II), Fe(III), Ag(I), Sc(III), and BF 3 results in lower reaction yields.…”

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confidence: 99%

Gallium and Indium Compounds in Homogeneous Catalysis

Dagorne

Fliedel

Frémont

2016

Encyclopedia of Inorganic and Bioinorganic Chemistry

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“…Pioneering research in this area was reported by Chiba group. 28,29 Manganese(III) salts, such as Mn(OAc) 3 , 30 are excellent one-electron oxidants, which have been widely employed to generate free radicals for cyclization reactions. Recently, Chiba and Narasaka demonstrated Mn(III)-catalyzed pyrrole formation from variously substituted vinyl azides and β -keto esters or 1,3-diketones (Scheme 16).…”

Section: Radical-initiated Reactions Of Vinyl Azidesmentioning

confidence: 99%

“…Recently, Chiba and Narasaka demonstrated Mn(III)-catalyzed pyrrole formation from variously substituted vinyl azides and β -keto esters or 1,3-diketones (Scheme 16). 28 The reaction is thought to proceed through the addition of manganese(III) enolate 91 to vinyl azide 19 via a radical pathway, giving iminyl radical 92 with the release of a reduced Mn(II) species and dinitrogen. The resulting iminyl radical 92 undergoes an intramolecular addition to a carbonyl group to give alkoxyl radical 93 , which is reduced by Mn(II) species to create Mn(III) alkoxide 95 (path a).…”

Section: Radical-initiated Reactions Of Vinyl Azidesmentioning

confidence: 99%

Reactivities of vinyl azides and their recent applications in nitrogen heterocycle synthesis

DiMagno

2015

Org. Biomol. Chem.

183

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Nitrogen heterocycles are abundant in natural products and pharmaceuticals. An emerging interest among synthetic chemists is to apply vinyl azides as a pivotal three-atom synthon for the construction of structurally complex and diverse N-heterocyclic skeletons. The unique features of the azide group connected to an alkene moiety permit vinyl azides to function as electrophiles, nucleophiles, or radical acceptors; their access to diverse reaction pathways provides great opportunities to generate highly reactive intermediates with often unusual or unconventional reactivities. This tutorial review will systematically illustrate the reactivities of vinyl azides and describe recent breakthroughs in the development of new transformations that create N-heterocycles.

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“…Herein, we developed as ingle-step general catalytic protocol for the high-yielding regioselective synthesis of 1,4,5-trisubstituted N-vinyl-1,2,3-triazoles and 1,4disubstituted N-vinyl-1,2,3-triazoles. [10] These drawbacks stimulated us to develop ag eneral catalytic protocol for the high-yielding regioselective synthesis of 1,4,5-/1,4-substituted N-vinyl-1,2,3-tria-zoles. Very little is known about the regioselective catalytic synthesis of functionalized N-vinyl-1,2,3-triazoles.…”

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confidence: 99%