Pd(0)-Catalyzed Cyclizative Carboboration of n-Iodo-1,6-diene (n = 1 or 2): Access to Structurally Complex Allylboronates and Alkylboronates.

A Pd(0)-catalyzed cyclizative carboboration reaction of n-iodo-1,6-diene (n = 1, 2) with B2pin2 has been developed. When 1-iodo-1,6-diene was employed as the substrate, a process of intramolecular 6,6-alkenylboration was achieved to deliver 6-membered cyclic allylborate. On the other hand, 2-iodo-1,6-diene was found to proceed via 2-cyclopropanation/1-boration, thus affording a (bicyclo[3.1.0]hexan-1-ylmethyl)borate product.