Aryl Halide Radical Clocks as Probes of Stannylene/Aryl Halide C-H Activation Rates

作者：Kavara Ajdin; Kheir Michael M; Kampf Jeff W; Holl Mark M Banaszak^*

来源：Journal of Inorganic and Organometallic Polymers and Materials, 2014, 24(1): 250-257.

DOI：10.1007/s10904-013-9990-y

• Stannylene
• C-H activation
• Radical clock

Using the radical cyclization induced by the reaction of (1) with 1-(but-3-en-1-yloxy)-2-iodobenzene, we have determined the rate of allylic and propargylic C-H activation to be 1.1 +/- A 0.2 x 10(8) M-1 s(-1). The rate of oxidative addition of aryl halide with 1 was estimated to be 10(7)-10(8) M-1 s(-1). The radical cyclization involving 1 and 1-(allyloxy)-2-iodobenzene proceeds quantitatively, indicating that the rate of cyclization (9.6 x 10(9) s(-1)) is faster than the rate of hydrocarbon/alkene/alkyne C-H abstraction.

• 出版日期2014-1