Direct, high-yielding, one-step synthesis of vic-diols from aryl alkynes

Ramachandran, P. Veeraraghavan; Drolet, Michael P.

doi:10.1016/j.tetlet.2018.01.041

Cited by 6 publications

(12 citation statements)

References 26 publications

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“…The disproportional cost of amine-boranes may also be a significant contributor to their underutilization . Recently, several cost-effective procedures to access amine-boranes , and their utility for hydroboration of alkenes and alkynes at higher temperatures , have been described.…”

Section: Introductionmentioning

confidence: 99%

“…In continuation of our ongoing study of amine-boranes, − ,, we undertook a thorough examination of the effect of Lewis acid (LA) catalysts to accelerate ketone hydroboration. The transition-metal-catalyzed dehydrogenation of amine-boranes, particularly ammonia borane, , was an initial concern.…”

Section: Introductionmentioning

confidence: 99%

“…The disproportional cost of amine-boranes may also be a significant contributor to their underutilization. 15 Recently, several costeffective procedures to access amine-boranes 16,17 and their utility for hydroboration of alkenes and alkynes at higher temperatures 18,19 have been described. Ammonia borane (AB, 1) has been reported to be superior to other amine-boranes, with aldehydes converted to alcohols faster than ketones in both aprotic and protic (MeOH−H 2 O) 9 solvents, including water.…”

Section: ■ Introductionmentioning

confidence: 99%

“…20 Past attempts to accelerate the reaction of amine-boranes include the addition of 1.2 equiv of BF 3 −Et 2 O to trimethylamine-borane (TMAB) for the reduction of 4-t-butylcyclohexanone, 5 increasing the acidity of the aqueous medium 6,7 or elevating the reaction temperature. 4 In continuation of our ongoing study of amine-boranes, [16][17][18][19]21,22 we undertook a thorough examination of the effect of Lewis acid (LA) catalysts to accelerate ketone hydroboration. The transition-metal-catalyzed dehydrogenation of amine-boranes, particularly ammonia borane, 23,24 was an initial concern.…”

Section: ■ Introductionmentioning

confidence: 99%

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TiCl₄-Catalyzed Hydroboration of Ketones with Ammonia Borane

2022

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Investigation of a variety of Lewis acids for the hydroboration-hydrolysis (reduction) of ketones with amine-boranes has revealed that catalytic (10 mol %) titanium tetrachloride (TiCl4) in diethyl ether at room temperature immensely accelerates the reaction of ammonia borane. The product alcohols are produced in good to excellent yields within 30 min, even with ketones which typically requires 24 h or longer to reduce under uncatalyzed conditions. Several potentially reactive functionalities are tolerated, and substituted cycloalkanones are reduced diastereoselectively to the thermodynamic product. A deuterium labeling study and 11B NMR analysis of the reaction have been performed to verify the proposed hydroboration mechanism.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

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TiCl₄-Catalyzed Hydroboration of Ketones with Ammonia Borane

2022

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“…This method was employed by the same group to convert alkynes into the corresponding vicinal diols. 29 In order to achieve a full dihydroboration two equivalents of ammonia borane proved to be necessary. As shown in Scheme 12, the hydroborated intermediate is then oxidized to the geminal diol in which the two hydroxyl groups displayed an antiarrangement.…”

Section: Reactions With Alkenes and Alkynesmentioning

confidence: 99%

Ammonia borane as a reducing agent in organic synthesis

et al. 2020

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Efficient Synthesis of Hydrobenzoin through NHC Catalysis: A Sustainable Approach for C−C Bond Formation

Sharma,

Mahantesh G,

Pradeep Kumar

et al. 2024

ChemistrySelect

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A facile and practical one‐pot synthesis of hydrobenzoin has been developed from the readily available aromatic aldehydes, under NHC catalysis. Basically, the present research elucidates a novel, sustainable approach for the synthesis of hydrobenzoin, capitalizing on the catalytic prowess of N‐heterocyclic carbene (NHC) and utilizing sodium borohydride (NaBH4) as an effective reducing partner in this one‐pot conversion. By harnessing the unique reactivity of NHCs, this methodology enables the efficient formation of C−C bonds, leading to the streamlined synthesis of hydrobenzoin with high yields while tolerating various functional groups. Furthermore, this catalytic system offers notable advantages in terms of atom economy, mild reaction conditions, and operational simplicity, making it a promising strategy for sustainable chemical synthesis. The detailed mechanistic insights provided herein shed light on the underlying catalytic pathways, facilitating a deeper understanding of the reaction mechanism. Overall, this study underscores the significant potential of NHC catalysis as a versatile tool for the sustainable synthesis of valuable organic compounds, thereby contributing to the advancement of green chemistry principles and the pursuit of environmentally benign chemical processes.

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Direct, high-yielding, one-step synthesis of vic-diols from aryl alkynes

Cited by 6 publications

References 26 publications

TiCl₄-Catalyzed Hydroboration of Ketones with Ammonia Borane

TiCl₄-Catalyzed Hydroboration of Ketones with Ammonia Borane

Ammonia borane as a reducing agent in organic synthesis

Efficient Synthesis of Hydrobenzoin through NHC Catalysis: A Sustainable Approach for C−C Bond Formation

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Direct, high-yielding, one-step synthesis of vic-diols from aryl alkynes

Cited by 6 publications

References 26 publications

TiCl4-Catalyzed Hydroboration of Ketones with Ammonia Borane

TiCl4-Catalyzed Hydroboration of Ketones with Ammonia Borane

Ammonia borane as a reducing agent in organic synthesis

Efficient Synthesis of Hydrobenzoin through NHC Catalysis: A Sustainable Approach for C−C Bond Formation

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Product

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TiCl₄-Catalyzed Hydroboration of Ketones with Ammonia Borane

TiCl₄-Catalyzed Hydroboration of Ketones with Ammonia Borane