Stereoselective Synthesis of Borylated 1,3‐Dienes by Synergistic Cu/Pd Catalysis

Abstract

My motto is… hard work always pays off. The thing Ilike most about my work is… when an idea turns into an excellent result. Chemistry is fun because… it provides an impressive toolkit that can be combined in many different manners fort he creative construction of an endless range of molecules with potential application in almost every single aspectofo ur lives.

Synergistic Pd/Cu Catalysis in Organic Synthesis

“…To illustrate the synthetic utility of this catalytic methodology, naturally occurring α‐( Z , E )‐homofarnesene 120 a and isosesquilavandulyl alcohol 120 b were prepared from simple starting materials. Subsequently, alkenyl bromides instead of allylic substrates were introduced into this catalytic system, affording the three‐component coupled products ( syn ‐1‐boron‐1,3‐dienes) …”

Boron and Silicon-Substituted 1,3-Dienes and Dienophiles and Their Use in Diels-Alder Reactions

“…Fananas-Mastral and Vazquez-Galinanes reported synergistic Cu/Pd-catalyzed couplings of alkynes ( 24 ) and bromoalkenes ( 25 ) to stereoselectively make 1-boron-substituted-1,3-dienes ( 26 ) ( Scheme 7 ) [ 11 ]. In one case, a boron diene thus produced was cross-coupled to produce a triene but no Diels-Alder chemistry of these dienes has yet been reported.…”

Synthesis of Conjugated Boron‐Enynes via cis‐Alkynylboration of Terminal Alkynes

“…Hou's group reported a Cu‐catalyzed boracarboxylation of phenylacetylene, only one example was given in this paper (Scheme , b) . Then, Cu‐ or Cu/Pd catalyzed allylboration and alkenylboration of terminal alkynes synthesis of skipped and conjuction dienes were realized (Scheme , c). Moreover, our group reported a regiodivergent copper‐catalyzed alkylboration of unactivated terminal alkynes, anti‐markovnikov and markovnikov alkylboration products were obtained by using two different ligands (Scheme , d).…”