Hydration of Olefins, Dienes, and Acetylenes via Hydroboration

Abstract

The hydroboration of olefins, dienes, and acetylenes involves the addition of a boron‐hydrogen bond to the carbon‐carbon multiple bond. This reaction provides a new, convenient route to the corresponding organoboranes and makes them readily available as intermediates in organic synthesis. One of the important reactions that the organoboranes undero is the rapid and essentially quantitative oxidation with alkaline hydrogen peroxide. The hydroboration of olefins involves a cis addition of the boron hydrogen bond, the boron atom becoming attached to the less substituted of the two olefinic carbon atoms of the double bond. This chapter surveys the available information on the hydration of olefins, dienes, acetylenes, and their derivatives by the hydroboration‐oxidation procedure.

(1-Bromovinyl)-MIDA boronate: a readily accessible and highly versatile building block for small molecule synthesis

“…7 While methods for the synthesis of 1,2-disubstituted alkenyl boronates are abundant, 8 the methods for the preparation of 1,1-disubstituted alkenyl boronates have been limited. 9 Recent methods for the preparation of these motifs include the copper catalyzed hydroboration of aryl and heteroaryl substituted alkynes.…”

New Reactivity Patterns in 3H‐Phosphaallene Chemistry [Aryl‐P=C=C(H)‐tBu]: Hydroboration of the C=C Bond, Deprotonation and Trimerisation

“…Hydroboration is a powerful method for the reduction of unsaturated compounds and the generation of functional molecules [16, 17] and has been applied also for the reduction of P−C double or triple bonds [18–20] . Phosphaalkenes, R‐P=CR’ 2 , afforded preferably products with P−H and C−B bonds [18, 19] .…”

A Modular Synthesis of Antitumor Macrolide (–)‐Lasonolide A†

“…However, the additional protection‐deprotection steps will dramatically decrease the synthetic efficacy. [ 22 ] The stability of borinate (the boron‐ate complex) generally encountered in the Brown hydroboration‐oxidation [ 23 ] inspired us to propose borane as a traceless protecting group. With the consideration of steric hindrance and stability, 9‐BBN was defined as the optimal reagent of choice.…”