Palladium(0)-catalyzed hydroboration of 1-buten-3-ynes: preparation of allenylboranes

Recent Advances in Organic Synthesis Using Transition Metal-Catalyzed Hydroborations

“…Since this seminal discovery, a considerable amount of research by the groups of Evans [9][10][11][12][13][14], Burgess [15][16][17][18][19][20][21], Baker and Marder [21][22][23], Sneddon [24][25][26], Hayashi [27,28], Suzuki [29,30] and Merola [31] has focussed on investigating the mechanism and scope of these catalyzed hydroboration reactions. While several excellent reviews have already been published in this area [32][33][34][35][36][37][38], the goal of this paper is to summarize the important findings in this area and discuss the use of this reaction in organic synthesis.…”

Site-Selective and Stereoselective trans-Hydroboration of 1,3-Enynes Catalyzed by 1,4-Azaborine-Based Phosphine–Pd Complex

“…7 In contrast to B , the corresponding carbonaceous phosphine ligand isostere C behaves more similarly to a monodentate phosphine such as PPh 3 in terms of hydroboration selectivity and yield, producing preferentially allenes via 1,4-hydroboration; bisphosphine ligands such as 1,2-bis(diphenylphosphino)ethane (dppe) furnish syn -hydroboration products exclusively. 8 Despite this promising preliminary result, our trans -hydroboration reaction still needed optimization with regard to yield and selectivity. More importantly, we wondered whether we could develop a trans -hydroboration protocol for internal enynes, a substrate class that is considered significantly more challenging ( vide infra ).…”

Some Synthetic Uses of Double‐Bonded Functional Groups

“…Hydroboration of a wide range of alkenes using catecholborane (and similar boranes), catalyzed by samarium(III) 136,137 , palladium 138,139 , iridium 140,141 and other transition metal and lanthanide complexes 142 145 , gives good to excellent yields of alcohols (equation 26). The process is regioselective and is dependent upon the catalyst used 146 .…”