Simmons-Smith Reaction

Schematic representation of the Simmons-Smith Reaction.

Mechanism of the Simmons-Smith Reaction

Mechanism of the Simmons-Smith Reaction

Original publication	J. Am. Chem. Soc.. 1958, 80, 532.
Reviews	Chem. Rev.. 2003, 103, 977. Comp. Org. Syn.. 1991, 4, 951. Comp. Org. Syn.. 1994, 1, 219. Org. React.. 1973, 20, 1. Org. React.. 2001, 58, 1.

Sample reactions

intermediate structure

Et2Zn, CH2I2

PhMe

0 °C, 30 min, 66%

intermediate structure

intermediate structure

Zn-Cu, CH2I2

Et2O

Reflux, 60 h, 78%

intermediate structure

intermediate structure

CH2I2, Zn-Ag

Et2O

RT, 18 h, 85%

intermediate structure

intermediate structure

Et2Zn, ClCH2I

DCE

0 °C, 40 min, 91%

intermediate structure

intermediate structure

Et2Zn, CH2Cl2

CH2Cl2

RT, 2 h, 86%

intermediate structure

intermediate structure

Zn-Ag

CH2Cl2, Et2O

0 °C, , 61%

intermediate structure