TY - JOUR
T1 - Hydrofunctionalisation of an Aromatic Triphosphabenzene
AU - Falconer, Rosalyn L.
AU - Zeng, Dihao
AU - Green, Michael
AU - Stephan, Douglas W.
AU - McGrady, John E.
AU - Russell, Christopher A.
PY - 2019/9/25
Y1 - 2019/9/25
N2 - The aromatic heterocycle 2,4,6‐tri‐tert‐butyl‐1,3,5‐triphosphabenzene reacts with a series of silanes, germanes and stannanes, with weaker E−H bonds reacting in an increasingly facile manner. All react by 1,4‐addition to give bicyclic products with diastereomeric ratios varying with the substrate. Density functional theory (DFT) calculations show that activation of the E−H bond occurs across the 1,4‐C/P axis of the triphosphabenzene, with the small energetic differences with respect to the stereochemistry of the addition offering insight into the experimentally observed diastereomeric ratios.
AB - The aromatic heterocycle 2,4,6‐tri‐tert‐butyl‐1,3,5‐triphosphabenzene reacts with a series of silanes, germanes and stannanes, with weaker E−H bonds reacting in an increasingly facile manner. All react by 1,4‐addition to give bicyclic products with diastereomeric ratios varying with the substrate. Density functional theory (DFT) calculations show that activation of the E−H bond occurs across the 1,4‐C/P axis of the triphosphabenzene, with the small energetic differences with respect to the stereochemistry of the addition offering insight into the experimentally observed diastereomeric ratios.
KW - hydrofunctionalisation
KW - hydrosilylation
KW - metal-free synthesis
KW - phosphorus
KW - triphosphabenzene
UR - http://www.scopus.com/inward/record.url?scp=85072211168&partnerID=8YFLogxK
U2 - 10.1002/chem.201903229
DO - 10.1002/chem.201903229
M3 - Article (Academic Journal)
C2 - 31414704
AN - SCOPUS:85072211168
VL - 25
SP - 12507
EP - 12511
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
SN - 0947-6539
IS - 54
ER -