Palladium(0)‐Catalyzed Cross‐Coupling of 1,1‐Diboronates with Vinyl Bromides and 1,1‐Dibromoalkenes

Abstractgem‐Diborylalkanes have emerged as efficient reagents for synthesizing organoboron compounds through selective C−C bond‐forming reactions. Activation of the 1,1‐diborylalkanes generates carbanions with enhanced stability that are able to react with a series of electrophiles, carbonyl compounds, imines and epoxides to promote formation of a new C−C bond. These new sets of reactions have become general for a wide range of substrates and they can be understood by alternative mechanisms that justify the potential use of these reagents. The formation of C–C(B) bonds can be achieved with chemo‐, diastereo‐ and enantioselectivity, because the nucleophilc α‐boryl or α‐diboryl carbanions attack in a stereoselective manner, by means of the catalyst involved. The synthesis of gem‐diborylalkanes has also been promoted by innovative methods and facilitates access to multiborylated reagents with different substituents and properties.magnified image

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Synthesis and Reactivity of 1,1‐Diborylalkanes towards C–C Bond Formation and Related Mechanisms

Miralles

2018

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Photocatalytic Chemodivergent Synthesis of α‐gem‐Dihalovinyl Ketones and Chromen‐2‐Ones from Monoalkynes

Liu

et al. 2022

Adv Synth Catal

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A general photocatalytic substrate‐controlled chemodivergent strategy starting from monoalkynes with polyhalomethanes such as BrCCl3 and CBr4 was develop, enabling Kharasch‐type addition/nucleophilic substitution cascade to selectively produce α‐gem‐dihalovinyl ketones and chromen‐2‐ones with moderate to good yields. Use of monoalkynes without additional nucleophilic sites furnished α‐gem‐dihalovinyl ketones through a Kharasch‐type addition and intermolecular allylic substitution cascade whereas the latter transformation of 2‐ethynylphenols allowed the full breaking of carbon‐halogen bonds of BrCX3 to access functionalized chromen‐2‐ones. The late‐stage application of these resulting α‐gem‐dihalovinyl ketones demonstrates the versatility of their derivatization.

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Synthesis of Branched Alkylboronates by Copper‐Catalyzed Allylic Substitution Reactions of Allylic Chlorides with 1,1‐Diborylalkanes

Kim

Park

et al. 2015

Angewandte Chemie

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Reported herein is acopper-catalyzed S N 2'-selective allylic substitution reaction using readily accessible allylic chlorides and 1,1-diborylalkanes,areaction which proceeds with chemoselective CÀBb ond activation of the 1,1-diborylalkanes.Inthe presence of acatalytic amount of [Cu(IMes)Cl] [IMes = 1,3-bis(2,4,6-trimethylphenyl)imidazole-2-ylidene] and LiOtBu as abase,arange of primary and secondary allylic chlorides undergo the S N 2'-selective allylic substitution reaction to produce branched alkylboronates.T he synthetic utilities of the obtained alkylboronates are also presented.

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Palladium(0)‐Catalyzed Cross‐Coupling of 1,1‐Diboronates with Vinyl Bromides and 1,1‐Dibromoalkenes

Cited by 28 publications

References 65 publications

Synthesis and Reactivity of 1,1‐Diborylalkanes towards C–C Bond Formation and Related Mechanisms

Synthesis and Reactivity of 1,1‐Diborylalkanes towards C–C Bond Formation and Related Mechanisms

Photocatalytic Chemodivergent Synthesis of α‐gem‐Dihalovinyl Ketones and Chromen‐2‐Ones from Monoalkynes

Synthesis of Branched Alkylboronates by Copper‐Catalyzed Allylic Substitution Reactions of Allylic Chlorides with 1,1‐Diborylalkanes

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