Palladium-Catalyzed Remote Diborylative Cyclization of Dienes with Diborons via Chain Walking

A novel method for catalytic remote bismetalation of alkene substrates by the addition of dimetal reagents is accomplished by using chain walking. In the presence of a palladium catalyst, the reaction of various 1,n-dienes and diborons were converted into cyclopentane derivatives with two boryl groups at remote positions via facile regioselective transformation of an unactivated sp(3) C-H bond to a C-B bond. Sequential construction of three distant bonds, which is difficult to achieve by any method, was accomplished for the reactions of 1,n-dienes (n >= 7).

Automated summary

A novel catalytic method using chain walking and dimetal reagents was developed for the remote bismetalation of alkene substrates, resulting in cyclopentane derivatives with two boryl groups at remote positions. The regioselective transformation of an unactivated sp(3) C-H bond to a C-B bond successfully achieved the sequential construction of three distant bonds for 1,n-dienes (n >= 7).