Hidden Boron Catalysis: Nucleophile-Promoted Decomposition of HBpin.

The continued development of hydroboration catalysts typifies the importance of this transformation as a testbed for catalytic activity and as a fundamental reaction for organic synthesis. Catalyti...

The Hidden Role of Boranes and Borohydrides in Hydroboration Catalysis

Organozinc compounds containing sp, sp2, and sp3 C–Zn moieties undergo transmetalation with pinacolborane (HBPin) to produce Zn–H species and organoboronate esters (RBPin). This Zn–C/H–B metathesis step is key to enabling zinc-catalyzed borylation reactions, and it is used in this work to develop both terminal alkyne C–H borylation and internal alkyne hydroboration. These two conversions can be combined in one pot to achieve the zinc-catalyzed conversion of terminal alkynes to 1,1-diborylated alkenes without isolation of the sensitive (to protodeboronation) alkynyl boronate ester intermediates. Mechanistic studies involving the isolation of intermediates, stoichiometric experiments, and DFT calculations all support mechanisms involving organozinc species that undergo metathesis with HBPin. Furthermore, zinc-catalyzed hydroboration can proceed via a hydrozincation step, which does not require any exogenous catalyst in contrast to all previously reported alkyne hydrozincations. Bulky N-heterocyclic carbenes...

/pdf/low-coordinate-nhc-zinc-hydride-complexes-catalyze-alkyne-c-4b8xw7fv5s.pdf

Low-Coordinate NHC–Zinc Hydride Complexes Catalyze Alkyne C–H Borylation and Hydroboration Using Pinacolborane

The addition of a B–H bond to an unsaturated bond (polarized or unpolarized) is a powerful and atom-economic tool for the synthesis of organoboranes. In recent years, s-block organometallics have appeared as alternative catalysts to transition-metal complexes, which traditionally catalyze the hydroboration of unsaturated bonds. Because of the recent and rapid development in the field of hydroboration of unsaturated bonds catalyzed by alkali (Li, Na, K) and alkaline earth (Mg, Ca, Sr, Ba) metals, we provide a detailed and updated comprehensive review that covers the synthesis, reactivity, and application of s-block metal catalysts in the hydroboration of polarized as well as unsaturated carbon–carbon bonds. Moreover, we describe the main reaction mechanisms, providing valuable insight into the reactivity of the s-block metal catalysts. Finally, we compare these s-block metal complexes with other redox-neutral catalytic systems based on p-block metals including aluminum complexes and f-block metal complexes of lanthanides and early actinides. In this review, we aim to provide a comprehensive, authoritative, and critical assessment of the state of the art within this highly interesting research area.

https://pubs.acs.org/doi/pdf/10.1021/acs.chemrev.1c00641

s-Block Metal Catalysts for the Hydroboration of Unsaturated Bonds

https://pubs.rsc.org/en/content/articlepdf/2018/cc/c7cc08214b

Lithium diamidodihydridoaluminates: bimetallic cooperativity in catalytic hydroboration and metallation applications

Simple, commercially available borane adducts, H 3 B·THF and H 3 B·SMe 2 , have been used to catalyse the hydroboration of alkynes and alkenes with pinacolborane to give the alkenyl and alkyl boronic esters, respectively. Alkynes and terminal alkenes underwent highly regioselective hydroboration to give the linear boronic ester products. Good functional group tolerance was observed for substrates bearing ester, amine, ether and halide substituents. This catalytic process shows comparable reactivity to transition-metal-catalysed hydroboration protocols.

/pdf/borane-catalysed-hydroboration-of-alkynes-and-alkenes-qgnontexkd.pdf

Borane-Catalysed Hydroboration of Alkynes and Alkenes

Here, we present a visible light-catalyzed hydroalkylation of aryl-alkenes affording C–C bonds using aryl-alkenes and alkyl iodides. We demonstrate the formation of various hydroalkylation products in excellent yields, with primary, secondary, and tertiary alkyl iodides being tolerated in the reaction. Mechanistic experiments reveal a pathway consisting of halogen atom transfer followed by a radical-polar crossover mechanism delivering the desired hydroalkylation products.

Photocatalytic Hydroalkylation of Aryl-Alkenes

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Borane-Catalysed Hydroboration of Alkynes and Alkenes

Photocatalytic Hydroalkylation of Aryl-Alkenes