N-Heterocyclic Carbene Boranes are Good Hydride Donors

Horn, Markus; Mayr, Herbert; Lacôte, Emmanuel; Merling, Everett; Deaner, Jordan D.; Wells, Sarah; McFadden, Timothy R.; Curran, Dennis P.

doi:10.1021/ol202836p

Cited by 81 publications

(70 citation statements)

References 25 publications

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“…56,57 Esse método notável utilizou etanol como solvente, catalisadores de ferro (III) como Fe(acac) 3 e Fe(dibm) 3 (acac = acetilacetonato, dibm = diisobutirilmetano) e fenilsilano como redutor, o que impacta em uma reação de baixo custo e que não necessita de exclusão de umidade ou oxigênio.…”

Section: Hidroaminação Formal De Olefinas Com Nitroarenos: Catálise Punclassified

“…Em vista disso, e da dificuldade de obter tal transformação com métodos conhecidos até então, Shenvi e colaboradores estudaram um protocolo de bis-hidroaminação formal. 74,75 A reação a partir da amina 153 envolve o uso de BH 3 •DMS e iodo molecular para realizar a hidroboração regiosseletiva das duplas trissubstituídas, gerando o intermediário 156. Para essa primeira etapa, foi observada ser essencial a adição lenta de iodo sob exclusão de luz, evitando assim a quebra da ligação potencialmente fotolábil B-I.…”

Section: Construção De Alcaloides Indolizidínicosunclassified

“…Para a síntese dessa classe de compostos, diversas metodologias para formação de ligação C-N foram desenvolvidas, dentre essas destacam-se N-alquilação, 1,2 aminação redutiva com compostos carbonílicos, 3,4 N-acilação 5,6 e acoplamento cruzado C-N. 7,8 Entre os métodos modernos para construção de compostos nitrogenados complexos, a hidroaminação de compostos insaturados vem ganhando destaque e desperta interesse da comunidade científica. 9,10 Essa abordagem impacta na economia de átomos do processo, o que é benéfico do ponto de vista da química verde.…”

Section: Introductionunclassified

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Avanços recentes na hidroaminação de compostos insaturados

Novaes¹,

Pastre²

2017

Quim. Nova

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publicado na web em 16/05/2017 RECENT ADVANCES ON HYDROAMINATION OF UNSATURATED COMPOUNDS. This review presents thermodynamics and kinetics aspects of the hydroamination reaction, recent advancements on this field for non-activated alkenes, alkynes and allenes, employing transition metal catalysis or organocatalysis, including activation by hydrogen bonding or Brønsted acids. Selected syntheses that contain a strategic hydroamination step will be discussed, and advancements on the asymmetric version will also be highlighted. The full coverage of scientific activity about hydroamination is beyond this review, therefore the examples presented are from the last ten years, except when there are historical reasons for the discussion of previous works.

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Section: Hidroaminação Formal De Olefinas Com Nitroarenos: Catálise Punclassified

Section: Construção De Alcaloides Indolizidínicosunclassified

Section: Introductionunclassified

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Avanços recentes na hidroaminação de compostos insaturados

Novaes¹,

Pastre²

2017

Quim. Nova

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“…Carbeneboranes have significant potential as reagents in organic synthesis and as initiators in polymer chemistry. [4][5][6][7][8][9][10][11][12] And the study of carbene-boranes as reactants has led to the synthesis of diverse stable compounds with unusual boron substituents and bonding patterns. [13][14][15][16][17][18][19][20][21][22][23] Curran group make heteroatomsubstituted NHC-boranes starting from the parent complex 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene borane and produce unusual functionalized NHC-borane compounds including boryl azides [R = 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene borane azide].…”

Section: Introductionmentioning

confidence: 99%

Density Functional Study on [3+2]-Dipolar Cycloaddition Reaction of the N-heterocyclic Carbene Boryl Azide with Olefins

Zhang¹,

Wang²,

Niu³

et al. 2014

Bulletin of the Korean Chemical Society

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The cycloaddition reactions of the N-heterocyclic carbene boryl azide with methyl acrylate, butenone, and hexafluoropropene have been investigated theoretically. Solvent effects on these reactions have been explored by calculation that included a polarizable continuum model (PCM) for the solvent (C6H6). The title reaction could produce 4-and 5-substituted 1,2,3-triazolines, respectively. The reaction systems have the higher chemical reactivity with the low barriers and could be favored. Yet the smaller differences have been found to occur in energetics, and the cycloaddition reactions occur for s-trans conformations over s-cis conformations. The calculations indicated that the cycloaddition reaction of the alkenes have certain regioselectivity.

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“…Instead, NHC-boranes have the rich chemistry of their own, providing unusual new boron compounds and reactive intermediates. Carbene-boranes are of interest as reagents in organic synthesis and as initiators in polymer chemistry [4][5][6][7][8][9][10][11][12]. There are many experimental reports about various stable carbene-boranes compounds which were synthesized with unusual boron substituents as reactants [13][14][15][16][17][18][19][20][21][22][23].…”

Section: Introductionmentioning

confidence: 99%

Theoretical study on reaction mechanism of an N-heterocyclic carbene boryl azide with electron-deficient alkynes and nitriles

2014

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A theoretical investigation of the [3?2] cycloaddition reaction of the NHC-boryl azide with alkynes and nitriles has been presented by using the DFT (B3LYP) method. Solvent effects on these reactions have been explored by calculation that included a polarizable continuum model (PCM) for the solvent (C 6 H 6 ). The title reaction could produce two different five-membered products (1,4-regioisomer and 1,5-regioisomer). The reaction pathway involves a one-step mechanism through a [3?2] addition where two nitrogen atoms of the N-heterocyclic carbene boryl azide adds to the C:A (A=C or N) bond to form two new C-N or N-N bonds. For alkynes, the reactions can take place more easily to give 1,4-regioisomer product, while the reactions proceed for nitriles along the 1,5-regioisomer pathway. The reaction systems have high chemical reactivity with low barriers and could be favored. The calculations indicated that the cycloaddition reaction of alkynes and nitriles has the better regioselectivity. Our computational results are good consistent with the experimental observations of Merling and co-workers for [3?2]-dipolar cycloaddition reaction of N-heterocyclic carbene boryl azide.

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N-Heterocyclic Carbene Boranes are Good Hydride Donors

Cited by 81 publications

References 25 publications

Avanços recentes na hidroaminação de compostos insaturados

Avanços recentes na hidroaminação de compostos insaturados

Density Functional Study on [3+2]-Dipolar Cycloaddition Reaction of the N-heterocyclic Carbene Boryl Azide with Olefins

Theoretical study on reaction mechanism of an N-heterocyclic carbene boryl azide with electron-deficient alkynes and nitriles

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