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Synthesis of 1-Alkynylboronates, 1,1-Diborylalkenes, and 1,1,1-Triborylalkanes: Challenges and Opportunities
Son Hoai Doan1, Vu Nguyen Tran1,2, Thanh Vinh Nguyen1
1School of Chemistry, University of New South Wales, Sydney, NSW, Australia.
Abstract:
In the field of organoboron chemistry, multi(boronate) esters have emerged as crucial intermediates, with various applications in synthetic chemistry, material technology, and life sciences. This mini-review discusses recent advancement in the synthesis of these versatile compounds, particularly alkynylboronates, 1,1-diborylalkenes, and 1,1,1-triborylalkanes, all of which are derived from easily accessible alkenes and alkynes. The article provides an in-depth analysis of these methodologies, delves into their mechanistic underpinnings, and emphasises their synthetic utility. Future research avenues and unresolved challenges in organoboron chemistry are also identified in this report, aiming to inspire further development of synthetic methods used in this area.
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03:08Hydroboration-Oxidation of Alkenes
02:47Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
02:36Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
02:27Preparation of Alkynes: Alkylation Reaction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
02:34Preparation of Alkynes: Dehydrohalogenation
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
02:15Preparation of Alcohols via Addition Reactions
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...