TY - JOUR
T1 - Elongated phosphoranes by C–C coupling of haloaroylmethylidenetriphenylphosphoranes
T2 - Synthesis and applications
AU - Thiemann, Thies
AU - Umeno, Kuniharu
AU - Wang, Jian
AU - Tabuchi, Yumiko
AU - Arima, Kazuya
AU - Watanabe, Masataka
AU - Tanaka, Yasuko
AU - Gorohmaru, Hideki
AU - Mataka, Shuntaro
PY - 2002/3/18
Y1 - 2002/3/18
N2 - Haloaroylmethylidenephosphoranes 3 can be subjected to Pd(0) mediated C–C coupling reactions to yield diaryl-, arylhetaryl-, dihetaryl, arylethenylaryl/hetaryl- and arylethynylaryl/hetaryl-carbonylmethylidenephosphoranes 4–9. Suzuki–Kumada reactions can also be run in a one-step procedure from (haloaroylmethyl)triphenylphosphonium bromides 2. Compounds 4–9 are air-stable phosphoranes which undergo formal Wittig-olefination reactions with aldehydes 10 under benzoic acid catalysis. C–C coupling reaction and Wittig olefination can also be performed in a one-step procedure. Preliminary experiments have been performed to carry out the synthesis on a solid support. Applications to the chain elongation and functionalisation of the chain terminus in a C-7 substituted estra-1,3,5(10)-triene 14 and a C-16 substituted estra-1,3,5(10),6-tetraene 12 are shown.
AB - Haloaroylmethylidenephosphoranes 3 can be subjected to Pd(0) mediated C–C coupling reactions to yield diaryl-, arylhetaryl-, dihetaryl, arylethenylaryl/hetaryl- and arylethynylaryl/hetaryl-carbonylmethylidenephosphoranes 4–9. Suzuki–Kumada reactions can also be run in a one-step procedure from (haloaroylmethyl)triphenylphosphonium bromides 2. Compounds 4–9 are air-stable phosphoranes which undergo formal Wittig-olefination reactions with aldehydes 10 under benzoic acid catalysis. C–C coupling reaction and Wittig olefination can also be performed in a one-step procedure. Preliminary experiments have been performed to carry out the synthesis on a solid support. Applications to the chain elongation and functionalisation of the chain terminus in a C-7 substituted estra-1,3,5(10)-triene 14 and a C-16 substituted estra-1,3,5(10),6-tetraene 12 are shown.
UR - http://www.scopus.com/inward/record.url?scp=0036026242&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0036026242&partnerID=8YFLogxK
U2 - 10.1039/b202745n
DO - 10.1039/b202745n
M3 - Article
AN - SCOPUS:0036026242
SN - 1472-7781
VL - 2
SP - 2090
EP - 2110
JO - Journal of the Chemical Society. Perkin Transactions 1
JF - Journal of the Chemical Society. Perkin Transactions 1
IS - 18
ER -