8 research outputs found
C(alkenyl)–H Activation via Six-Membered Palladacycles: Catalytic 1,3-Diene Synthesis
A catalytic
method to prepare highly substituted 1,3-dienes from
two different alkenes is described using a directed, palladiumÂ(II)-mediated
CÂ(alkenyl)–H activation strategy. The transformation exhibits
broad scope across three synthetically useful substrate classes masked
with suitable bidentate auxiliaries (4-pentenoic acids, allylic alcohols,
and bishomoallylic amines) and tolerates internal nonconjugated alkenes,
which have traditionally been a challenging class of substrates in
this type of chemistry. Catalytic turnover is enabled by either MnO<sub>2</sub> as the stoichiometric oxidant or co-catalytic CoÂ(OAc)<sub>2</sub> and O<sub>2</sub> (1 atm). Experimental and computational
studies were performed to elucidate the preference for CÂ(alkenyl)–H
activation over other potential pathways. As part of this effort,
a structurally unique alkenylpalladiumÂ(II) dimer was isolated and
characterized
C(alkenyl)–H Activation via Six-Membered Palladacycles: Catalytic 1,3-Diene Synthesis
A catalytic
method to prepare highly substituted 1,3-dienes from
two different alkenes is described using a directed, palladiumÂ(II)-mediated
CÂ(alkenyl)–H activation strategy. The transformation exhibits
broad scope across three synthetically useful substrate classes masked
with suitable bidentate auxiliaries (4-pentenoic acids, allylic alcohols,
and bishomoallylic amines) and tolerates internal nonconjugated alkenes,
which have traditionally been a challenging class of substrates in
this type of chemistry. Catalytic turnover is enabled by either MnO<sub>2</sub> as the stoichiometric oxidant or co-catalytic CoÂ(OAc)<sub>2</sub> and O<sub>2</sub> (1 atm). Experimental and computational
studies were performed to elucidate the preference for CÂ(alkenyl)–H
activation over other potential pathways. As part of this effort,
a structurally unique alkenylpalladiumÂ(II) dimer was isolated and
characterized
C(alkenyl)–H Activation via Six-Membered Palladacycles: Catalytic 1,3-Diene Synthesis
A catalytic
method to prepare highly substituted 1,3-dienes from
two different alkenes is described using a directed, palladiumÂ(II)-mediated
CÂ(alkenyl)–H activation strategy. The transformation exhibits
broad scope across three synthetically useful substrate classes masked
with suitable bidentate auxiliaries (4-pentenoic acids, allylic alcohols,
and bishomoallylic amines) and tolerates internal nonconjugated alkenes,
which have traditionally been a challenging class of substrates in
this type of chemistry. Catalytic turnover is enabled by either MnO<sub>2</sub> as the stoichiometric oxidant or co-catalytic CoÂ(OAc)<sub>2</sub> and O<sub>2</sub> (1 atm). Experimental and computational
studies were performed to elucidate the preference for CÂ(alkenyl)–H
activation over other potential pathways. As part of this effort,
a structurally unique alkenylpalladiumÂ(II) dimer was isolated and
characterized
C(alkenyl)–H Activation via Six-Membered Palladacycles: Catalytic 1,3-Diene Synthesis
A catalytic
method to prepare highly substituted 1,3-dienes from
two different alkenes is described using a directed, palladiumÂ(II)-mediated
CÂ(alkenyl)–H activation strategy. The transformation exhibits
broad scope across three synthetically useful substrate classes masked
with suitable bidentate auxiliaries (4-pentenoic acids, allylic alcohols,
and bishomoallylic amines) and tolerates internal nonconjugated alkenes,
which have traditionally been a challenging class of substrates in
this type of chemistry. Catalytic turnover is enabled by either MnO<sub>2</sub> as the stoichiometric oxidant or co-catalytic CoÂ(OAc)<sub>2</sub> and O<sub>2</sub> (1 atm). Experimental and computational
studies were performed to elucidate the preference for CÂ(alkenyl)–H
activation over other potential pathways. As part of this effort,
a structurally unique alkenylpalladiumÂ(II) dimer was isolated and
characterized
C(alkenyl)–H Activation via Six-Membered Palladacycles: Catalytic 1,3-Diene Synthesis
A catalytic
method to prepare highly substituted 1,3-dienes from
two different alkenes is described using a directed, palladiumÂ(II)-mediated
CÂ(alkenyl)–H activation strategy. The transformation exhibits
broad scope across three synthetically useful substrate classes masked
with suitable bidentate auxiliaries (4-pentenoic acids, allylic alcohols,
and bishomoallylic amines) and tolerates internal nonconjugated alkenes,
which have traditionally been a challenging class of substrates in
this type of chemistry. Catalytic turnover is enabled by either MnO<sub>2</sub> as the stoichiometric oxidant or co-catalytic CoÂ(OAc)<sub>2</sub> and O<sub>2</sub> (1 atm). Experimental and computational
studies were performed to elucidate the preference for CÂ(alkenyl)–H
activation over other potential pathways. As part of this effort,
a structurally unique alkenylpalladiumÂ(II) dimer was isolated and
characterized
Catalytic, Enantioselective Synthesis of Allenyl Boronates
A method
to achieve enantioselective 1,4-hydroboration of terminal
and internal enynes to access allenyl boronates under CuH catalysis
is described. The reaction typically proceeds in a highly stereoselective
manner and tolerates an array of synthetically useful functional groups.
The utility of the enantioenriched allenyl boronate products is demonstrated
through several representative downstream derivatizations
Catalytic, Enantioselective Synthesis of Allenyl Boronates
A method
to achieve enantioselective 1,4-hydroboration of terminal
and internal enynes to access allenyl boronates under CuH catalysis
is described. The reaction typically proceeds in a highly stereoselective
manner and tolerates an array of synthetically useful functional groups.
The utility of the enantioenriched allenyl boronate products is demonstrated
through several representative downstream derivatizations
Catalytic, Enantioselective Synthesis of Allenyl Boronates
A method to achieve enantioselective 1,4-hydroboration of terminal enynes to access allenyl boronates under CuH catalysis is described. The reaction typically proceeds in a highly stereoselective manner and tolerates an array of synthetically useful functional groups. The utility of the enantioenriched allenyl boronate products is demonstrated through several representative downstream derivatizations