Iridium‐Catalyzed Distal Hydroboration of Aliphatic Internal Alkenes

Iron complexes [BIAN]Fe(I)(η6‐toluene) (M1) and [BIAN]FeCl2 (M2) (BIAN=bis(2,6‐diisopropylaniline)acenaphthene) were found to be viable catalysts for the regioselective hydroboration of alkynes and alkenes. The hydroboration of alkynes and alkenes in the presence of HBpin and an activator at 70 °C afforded linear vinyl and alkyl boronic esters, respectively. Selectivity up to 98% was observed for alkyl boronic esters and exclusive formation of trans product was observed for vinyl boronic esters.

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Hydroboration of Alkenes and Alkynes Employing Earth‐Abundant Metal Catalysts

Singh

Shafiei‐Haghighi

Smith

et al. 2019

Asian J Org Chem

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H₂‐Acceptorless Dehydrogenative Boration and Transfer Boration of Alkenes Enabled by Zirconium Catalyst

Shi

2019

Angewandte Chemie

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The first example of an efficient and direct dehydrogenative boration of alkenes for vinyl boronate ester synthesis was achieved using a zirconium catalyst. Our methodology avoids using precious transition metals, additional hydrogen acceptors, high temperatures, and long reaction times, which were required to overcome the reducing ability of borane, to give alkyl boronate esters. Detailed mechanistic studies revealed a reversible reaction pathway and further suggested applying the zirconium complex as a “shuttle catalyst” for transfer boration, which thus sidesteps the use of relatively sensitive borane.

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Zirconium‐Catalyzed Atom‐Economical Synthesis of 1,1‐Diborylalkanes from Terminal and Internal Alkenes

Wang

Cui

et al. 2020

Angewandte Chemie

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A general and atom‐economical synthesis of 1,1‐diborylalkanes from alkenes and a borane without the need for an additional H2 acceptor is reported for the first time. The key to our success is the use of an earth‐abundant zirconium‐based catalyst, which allows a balance of self‐contradictory reactivities (dehydrogenative boration and hydroboration) to be achieved. Our method avoids using an excess amount of another alkene as an H2 acceptor, which was required in other reported systems. Furthermore, substrates such as simple long‐chain aliphatic alkenes that did not react before also underwent 1,1‐diboration in our system. Significantly, the unprecedented 1,1‐diboration of internal alkenes enabled the preparation of 1,1‐diborylalkanes.

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Iridium‐Catalyzed Distal Hydroboration of Aliphatic Internal Alkenes

Abstract: Scheme 1. Transition-metal-catalyzed regioselective hydroboration of aliphatic internal alkenes.D G= directing group.

Cited by 11 publications

References 76 publications

Hydroboration of Alkenes and Alkynes Employing Earth‐Abundant Metal Catalysts

Hydroboration of Alkenes and Alkynes Employing Earth‐Abundant Metal Catalysts

H₂‐Acceptorless Dehydrogenative Boration and Transfer Boration of Alkenes Enabled by Zirconium Catalyst

Zirconium‐Catalyzed Atom‐Economical Synthesis of 1,1‐Diborylalkanes from Terminal and Internal Alkenes

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Iridium‐Catalyzed Distal Hydroboration of Aliphatic Internal Alkenes

Abstract: Scheme 1. Transition-metal-catalyzed regioselective hydroboration of aliphatic internal alkenes.D G= directing group.

Cited by 11 publications

References 76 publications

Hydroboration of Alkenes and Alkynes Employing Earth‐Abundant Metal Catalysts

Hydroboration of Alkenes and Alkynes Employing Earth‐Abundant Metal Catalysts

H2‐Acceptorless Dehydrogenative Boration and Transfer Boration of Alkenes Enabled by Zirconium Catalyst

Zirconium‐Catalyzed Atom‐Economical Synthesis of 1,1‐Diborylalkanes from Terminal and Internal Alkenes

Contact Info

Product

Resources

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H₂‐Acceptorless Dehydrogenative Boration and Transfer Boration of Alkenes Enabled by Zirconium Catalyst