Multi-step reaction with 13 steps
1.1: (S,RFe)-Josiphos*CuBr complex / various solvent(s); diethyl ether / 0.33 h / -75 °C
1.2: 95 percent / various solvent(s); diethyl ether / 17 h / -75 °C
2.1: Et3SiH / Pd-C / CH2Cl2 / 20 °C
3.1: 1.491 g / CH2Cl2 / 24 h / Heating
4.1: (S,RFe)-Josiphos*CuBr complex / various solvent(s); diethyl ether / 0.33 h / -75 °C
4.2: 90 percent / various solvent(s); diethyl ether / 17 h / -75 °C
5.1: Et3SiH / Pd-C / CH2Cl2 / 20 °C
6.1: 214 mg / CH2Cl2 / 24 h / Heating
7.1: (S,RFe)-Josiphos*CuBr complex / various solvent(s); diethyl ether / 0.33 h / -75 °C
7.2: 85 percent / various solvent(s); diethyl ether / 17 h / -75 °C
8.1: Et3SiH / Pd-C / CH2Cl2 / 20 °C
9.1: 1.102 g / CH2Cl2 / 24 h / Heating
10.1: (S,RFe)-Josiphos*CuBr complex / various solvent(s); diethyl ether / 0.17 h / -75 °C
10.2: 88 percent / various solvent(s); diethyl ether / 17 h / -75 °C
11.1: 95 percent / DIBAL-H / tetrahydrofuran; CH2Cl2 / -20 °C
12.1: 95 percent / pyridine / CH2Cl2 / 24 h / 20 °C
13.1: magnesium / tetrahydrofuran / 1 h / 45 °C
13.2: 80 percent / CuBr*SMe2 / tetrahydrofuran / 24 h / 20 °C
With
pyridine; triethylsilane; diisobutylaluminium hydride; magnesium;
palladium on activated charcoal; (S,RFe)-Josiphos*CuBr;
In
tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1039/b612593j