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Updated: May 14, 2026

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
12:27

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

Published on: September 8, 2013

終端アルキンの触媒性脱水化ボリレーションは,イリジウムのSiNNピンサー複合体によって行われる

Chun-I Lee1, Jia Zhou, Oleg V Ozerov

  • 1Department of Chemistry, Texas A&M University, 3255 TAMU, College Station, Texas 77842, United States.

Journal of the American Chemical Society
|February 5, 2013
PubMed
まとめ

末端アルキンの化学選択的触媒性脱水酸化ボリル化が可能になりました. ユニークなSiNNピンサーリガンドを持つ新しいイリジウム触媒は,C-H結合からアルキニルボロナートの効率的な合成を可能にします.

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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
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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.
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Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
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Hydroboration-Oxidation of Alkenes

In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
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Preparation of Alkynes: Alkylation Reaction

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Electrophilic Addition to Alkynes: Halogenation

Introduction
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