Chemistry - A European Journal
10.1002/chem.201602332
COMMUNICATION
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2 2
[17] Other solvents were tested (DMF, MeCN, THF, toluene) but CH Cl led
to the best results. The reaction was carried out at different
temperatures (from RT to 100 °C) but the highest yield of 2a was
observed at 60 °C, see Supporting Information for details.
[
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[
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·H
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[20] In the case of 1j, stabilization of ruthenacycle intermediate [Ru]-j by
chelation may result in an inefficient catalyst turn-over, but attempts to
observe [Ru]-j by NMR failed. Interestingly, substrate 1p possessing a
N-Boc-indol-3-yl group was unreactive (potential formation ruthenacycle
[Ru]-p), whereas the N-Me analog 1n underwent macrocyclization. The
reason why macrocyclization of enyne 1k operates may be due to a
more favorable equilibrium between the chelated/non-chelated
ruthenacycles [Ru]-k/[Ru]-k’.
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[
Ru]-j
OMe
[Ru]-p
[
[
[
8]
O
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N
[Ru]
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1