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. Author manuscript; available in PMC: 2016 Jun 3.
Published in final edited form as: Tetrahedron Lett. 2015 Jun 3;56(23):3546–3549. doi: 10.1016/j.tetlet.2015.01.075

Table 1.

Optimization of APKR for the synthesis of dienone 10a.

graphic file with name nihms-661126-f0004.jpg
Entry Rh(I) Catalyst Loading (mol%) Temperature (°C) Concentration (M) Time Yield (%)
1 [Rh(CO)2Cl]2 15 90 0.1 1.5 h 27
2 [Rh(CO)2Cl]2 15a 90 0.1 1.5 h 32
3 [Rh(CO)2Cl]2 15a 90 0.01 1.5 h 53
4 [Rh(CO)2Cl]2 15a 110 0.01 25 min 57
5 [Rh(CO)2Cl]2 10a 110 0.01b c 81
6 [Rh(CO)2Cl]2 5a 110 0.01b c 80
7 [Rh(CO)2Cl]2 2a 110 0.01b c 62
8 [Rh(CO)2Cl]2 1a 110 0.01b c 63
9 [Rh(CO)(dppp)2]Cl 10a 110 0.1 21 hd 27
10 [Rh(CO)(dppp)2]Cl 10a 110 0.01 21 hd 46
11 [Rh(CO)Cl(dppp)]2 10a 110 0.01 6 h 29
a

Triphenylphosphine polymer bound was used in the reaction work up.

b

Syringe pump addition of allene-yne to Rh(I) solution was utilized.

c

Dropwise addition over 1.5 h and an additional 15 min of reaction time.

d

Reaction was not monitored between 8-21 h.