TY - JOUR
T1 - Synthesis of crowded triarylphosphines carrying functional sites
AU - Sasaki, Shigeru
AU - Murakami, Fumiki
AU - Murakami, Midori
AU - Watanabe, Mariko
AU - Kato, Kiyotoshi
AU - Sutoh, Katsuhide
AU - Yoshifuji, Masaaki
N1 - Funding Information:
Financial support by Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology (Nos. 15550025 and 1330409) is gratefully acknowledged. The authors also thank the Instrumental Analysis Center for Chemistry, Graduate School of Science, Tohoku University, for measurement of 600 MHz NMR, mass spectra, and elemental analysis.
PY - 2005/5/16
Y1 - 2005/5/16
N2 - 4,4′-Diphosphinobiaryls and 1,3- and 1,4-borylphosphinobenzenes carrying crowded triarylphosphine moieties were synthesized by reaction of the corresponding diarylchlorophosphine with an arylcopper(I) reagent. Intramolecular interaction of the phosphorus redox center with the other phosphorus or the boron redox center was investigated by cyclic voltammetry. 4,4′-Diphosphinobiaryls displayed two-step reversible redox waves with slight differences of the oxidation potentials due to weak interaction between two phosphorus redox centers across 4,4′-biarylene linkage. Borylphosphinobenzenes showed two step redox waves corresponding to oxidation at the phosphorus and reduction at the boron. Although significant interaction between the phosphorus and boron redox centers was not observed in the cyclic voltammograms due to large difference of the redox potentials between phosphorus and boron redox centers, an absorption due to weakly interacting phosphorus and boron was observed in the UV-Vis spectrum of the 1,4-borylphosphinobenzene.
AB - 4,4′-Diphosphinobiaryls and 1,3- and 1,4-borylphosphinobenzenes carrying crowded triarylphosphine moieties were synthesized by reaction of the corresponding diarylchlorophosphine with an arylcopper(I) reagent. Intramolecular interaction of the phosphorus redox center with the other phosphorus or the boron redox center was investigated by cyclic voltammetry. 4,4′-Diphosphinobiaryls displayed two-step reversible redox waves with slight differences of the oxidation potentials due to weak interaction between two phosphorus redox centers across 4,4′-biarylene linkage. Borylphosphinobenzenes showed two step redox waves corresponding to oxidation at the phosphorus and reduction at the boron. Although significant interaction between the phosphorus and boron redox centers was not observed in the cyclic voltammograms due to large difference of the redox potentials between phosphorus and boron redox centers, an absorption due to weakly interacting phosphorus and boron was observed in the UV-Vis spectrum of the 1,4-borylphosphinobenzene.
KW - Biaryl
KW - Cyclic voltammetry
KW - Triarylborane
KW - Triarylphosphine
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U2 - 10.1016/j.jorganchem.2004.10.031
DO - 10.1016/j.jorganchem.2004.10.031
M3 - Conference article
AN - SCOPUS:17944383225
VL - 690
SP - 2664
EP - 2672
JO - Journal of Organometallic Chemistry
JF - Journal of Organometallic Chemistry
SN - 0022-328X
IS - 10
T2 - 16th International Conference on Phosphorus Chemistry ICPC
Y2 - 4 July 2004 through 9 July 2004
ER -