Phosphine‐Catalyzed 1,2‐<i>cis</i>‐Diboration of 1,3‐Butadiynes

Li, Weipeng; Ricker, Robert; Lok Chan, Ka; Fung Lau, Pak; Buchbinder, Nicklas W.; Krebs, Johannes; Friedrich, Alexandra; Lin, Zhenyang; Santos, Webster L.; Radius, Udo; Marder, Todd B.

doi:10.1002/chem.202401235

Chemistry A European J

2024

DOI: 10.1002/chem.202401235

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Phosphine‐Catalyzed 1,2‐cis‐Diboration of 1,3‐Butadiynes

Weipeng Li,

Robert Ricker,

Ka Lok Chan

et al.

Abstract: Trialkyl phosphines PMe3 and PEt3 catalyze the 1,2‐cis‐diboration of 1,3‐butadiynes to give 1,2‐diboryl enynes. The products were utilized to synthesize 1,1,2,4‐tetraaryl enynes using a Suzuki‐Miyaura protocol and can readily undergo proto‐deborylation.

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A Mild and General trans-Diboration of Both Terminal and Internal Propargyl Alcohols

Gu,

Chen,

Wang

et al. 2024

Org. Lett.

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A practical and efficient trans-diboration of propargyl alcohols was accomplished using sodium hydride (NaH) as a base in N,N-dimethylformamide at room temperature. The mild reaction conditions demonstrate general applicability, facilitating the successful conversion of both terminal and internal propargyl alcohols with diverse structures and functional groups into highly functionalized alkenediboronates [4-borylated 1,2-oxaborol-2(5H)-oles]. The resulting products, which incorporate two boron groups, can be selectively activated and subjected to stepwise transformations, thereby providing an effective platform for synthesizing a wide range of structurally diverse trisubstituted alkenes.

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A Mild and General trans-Diboration of Both Terminal and Internal Propargyl Alcohols

Gu,

Chen,

Wang

et al. 2024

Org. Lett.

View full text Add to dashboard Cite

show abstract

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Phosphine‐Catalyzed 1,2‐cis‐Diboration of 1,3‐Butadiynes

Abstract: Trialkyl phosphines PMe3 and PEt3 catalyze the 1,2‐cis‐diboration of 1,3‐butadiynes to give 1,2‐diboryl enynes. The products were utilized to synthesize 1,1,2,4‐tetraaryl enynes using a Suzuki‐Miyaura protocol and can readily undergo proto‐deborylation.

Cited by 1 publication

References 78 publications

A Mild and General trans-Diboration of Both Terminal and Internal Propargyl Alcohols

A Mild and General trans-Diboration of Both Terminal and Internal Propargyl Alcohols

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