Cited by Metal-free catalytic hydroboration of imine with pinacolborane using a pincer-type phosphorus compound: mechanistic insight and improvement of the reaction

X-type silyl ligands for transition-metal catalysis DOI

Jihui Gao,

Yicong Ge,

Chuan He

et al.

Chemical Society Reviews, Journal Year: 2024, Volume and Issue: 53(9), P. 4648 - 4673

Published: Jan. 1, 2024

This review summarizes the developments of X-type silyl ligands for transition-metal catalysis, elucidating unique features σ-donating ability and trans -influence silyl–metal catalysts.

Language: Английский

Citations

Zinc Catalyzed Hydroelementation (HE; E = B, C, N, and O) of Carbodiimides: Intermediates Isolation and Mechanistic Insights DOI

Rajata Kumar Sahoo,

A. Ganesh Patro,

Nabin Sarkar

et al.

Organometallics, Journal Year: 2023, Volume and Issue: 42(14), P. 1746 - 1758

Published: March 15, 2023

The conjugated bis-guanidinate (CBG) supported zinc hydride, [{LZnH}2; L = {(ArHN)(ArN)-C═N–C═(NAr)(NHAr); Ar 2,6-Et2-C6H3}] (1) (pre)-catalyzed addition of E–H (E B, C, N, and O) to carbodiimides is presented. Compound 1 catalyzed the reduction with pinacolborane (HBpin), terminal alkynes, primary amines, alcohols, gave a series N-boryl formamidines, propiolamidines, guanidines, isoureas high conversions. All these reactions display good tolerance functional groups. These proceeded through active catalysts intermediate amidinate (Zn-1, Zn-1′, Zn-3), alkynyl (Zn-2, Zn-2′), anilide (Zn-4), alkoxide (Zn-5) complexes, which have been characterized by multinuclear NMR HRMS analyses. Moreover, compounds Zn-2′, Zn-4, Zn-5 were confirmed single-crystal X-ray diffraction studies. Complete catalytic cycles proposed based on well-defined intermediates stoichiometric experiments.

Language: Английский

Citations

Visible-light-driven PhSSPh-catalysed regioselective hydroborylation of α,β-unsaturated carbonyl compounds with NHC-boranes DOI

Xinghua Liu,

Yujing Shen,

Cheng Lu

et al.

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(60), P. 8380 - 8383

Published: Jan. 1, 2022

A photo-induced transition-metal-free regioselective hydroborylation of α,β-unsaturated carbonyl compounds is developed. The PhSSPh reagent was employed as the photocatalyst, and NHC-BH3 used boron source. This transformation shows a broad substrate scope provides wide range α-borylcarbonyl molecules in good to excellent yields.

Language: Английский

Citations

A N‐Heterocyclic Carbene‐Supported Zinc Catalyst for the 1,2‐Regioselective Hydroboration of N‐Heteroarenes DOI

Sumana Mondal,

Tejender Singh,

Sudip Baguli

et al.

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 29(38)

Published: April 20, 2023

A fluorenyl-tethered N-heterocyclic carbene LH (LH=[(Flu)H-(CH2 )2 -NHCDipp ]) and its monoanionic version L- are explored in complexation with zinc towards the hydroboration of N-heteroarenes, carbonyl, ester, amide, nitrile under ambient condition. The N-heteroarenes exhibit high 1,2-regioselectivity which is justified by computational analyses. relative rates differently p-substituted (electron donating vs. withdrawing) pyridines also addressed. monodentate offers a better catalytic activity than chelating for steric reasons despite both giving three-coordinate complexes. mechanism involves Zn-H species at heart these processes trapped Ph2 CO. Computational studies suggest that barrier to form hydride complex comparable required following transfer pyridine.

Language: Английский

Citations

Bis(1‐Methyl‐ortho‐Carboranyl)Borane DOI

Manjur O. Akram, John R. Tidwell, Jason L. Dutton

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(34)

Published: June 20, 2023

The Lewis superacid, bis(1-methyl-ortho-carboranyl)borane, is rapidly accessed in two steps. It a very effective hydroboration reagent capable of B-H addition to alkenes, alkynes, and cyclopropanes. To date, this the first identified superacidic secondary borane most reactive neutral reagent.

Language: Английский

Citations

Secondary-sphere preorganization enables nickel-catalyzed nitrile hydroboration DOI

Medina Afandiyeva, Xijue Wu, William W. Brennessel

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(90), P. 13450 - 13453

Published: Jan. 1, 2023

Herein, we describe nickel-catalyzed nitrile hydroboration with pinacolborane, wherein a tethered NHC-pyridonate ligand enables efficient catalysis (5 mol% [Ni], ≤6 h reaction time) at room temperature. Mechanistic studies, including isolation of the catalytically relevant intermediates, shed light on cooperative role in activating both reagents simultaneously.

Language: Английский

Citations

Fluorenyl-tethered N-heterocyclic carbene: An effective ancillary support for heteroleptic magnesium organometallics DOI

Sumana Mondal,

Subham Sarkar,

Dibyendu Mallick

et al.

Polyhedron, Journal Year: 2024, Volume and Issue: 251, P. 116849 - 116849

Published: Jan. 21, 2024

Language: Английский

Citations

Green synthesis of pyrrolo[1,2-α]quinoxalines by palladium-catalyzed transfer hydrogenation with nitriles as carbon synthons DOI

Xing Sheng,

Jiayi Xian,

Shuting Liu

et al.

Journal of Catalysis, Journal Year: 2023, Volume and Issue: 421, P. 156 - 161

Published: March 15, 2023

Language: Английский

Citations

A robust Zintl cluster for the catalytic reduction of pyridines, imines and nitriles DOI

Bono van IJzendoorn, Jessica B. M. Whittingham, George F. S. Whitehead

et al.

Dalton Transactions, Journal Year: 2023, Volume and Issue: 52(38), P. 13787 - 13796

Published: Jan. 1, 2023

Despite p-block clusters being known for over a century, their application as catalysts to mediate organic transformations is underexplored. Here, the boron functionalized [P7] cluster [(BBN)P7]2- ([1]2-; BBN = 9-borabicyclo[3.3.1]nonane) applied in dearomatized reduction of pyridines, well hydroboration imines and nitriles. These afford amine products, which are important precursors pharmaceuticals, agrochemicals, polymers. Catalyst [1]2- has high stability these reductions: recycling nine times quinoline led virtually no loss catalyst performance. The can also be recycled between two different transformations, again with competency. mechanism pyridine was probed experimentally using variable time normalization analysis, computationally density functional theory. This work demonstrates that Zintl nitrogen containing substrates transition metal-free manner.

Language: Английский

Citations

Mixed Lithium–Aluminum Hydrides Bearing Ar-Bian Ligands: Reactivity Toward Heteroallenes DOI

Tatyana S. Koptseva,

Andrey A. Bazanov,

Alexandra A. Skatova

et al.

Organometallics, Journal Year: 2024, Volume and Issue: 43(13), P. 1438 - 1446

Published: June 13, 2024

The reactivity of [(dpp-Bian)Al(H)2Li(THF)3] (1) (dpp-Bian = 1,2-bis[(2,6-diisopropylphenyl)imino]acenaphthene) and [(ArBIG-Bian)Al(H)2Li(THF)4] (2) (ArBIG-Bian 1,2-bis[(2,6-dibenzhydryl-4-methylphenyl)imino]acenaphthene) toward isocyanates carbodiimides has been investigated. A treatment 1 with tert-buthylisocyanate affords the formimidate derivative [(dpp-Bian)Al(μ2-OC(H)NtBu)2Li(THF)] (3). related [(ArBIG-Bian)Al(μ2-OC(H)NCy)2Li(THF)] (4) [(ArBIG-Bian)Al((μ-OC(H)NPh)Li(THF)3)(OC(H)NPh)] (5) have obtained by reacting 2 cyclohexyl phenylisocyanates, respectively. Cyclohexylcarbodiimide reacts to give corresponding amidinate derivatives [(dpp-Bian)Al(CyNC(H)NCy)(μ-CyNC(H)NCy)Li(THF)2] (6) [(ArBIG-Bian)Al(CyNC(H)NCy)][Li(DME)3] (7). Complexes 3-7 were characterized IR NMR spectroscopy. molecular structures compounds determined single-crystal X-ray analysis. Both serve well as catalysts in hydroboration pinacolborane (HBpin).

Language: Английский

Citations