Copper‐Catalyzed Regioselective Borocarbonylative Coupling of Unactivated Alkenes with Alkyl Halides: Synthesis of β‐Boryl Ketones

Abstract

The borocarbonylative coupling of unactivated alkenes with alkyl halides remains a challenge. In this communication, a Cu‐catalyzed borocarbonylative coupling of unactivated alkenes with alkyl halides for the synthesis of β‐boryl ketones has been developed. A broad range of β‐boryl ketone derivatives was prepared in moderate to excellent yields with complete regioselectivity.

DFT calculations reveal the origin of controllable synthesis of β-boronyl carbonyl compounds from Cu/Pd-cocatalyzed four-component borocarbonylation of vinylarenes

“…However, we note that Wu's group also reported a similar four-component borocarbonylation of unactivated alkenes with alkyl halides to synthesize β-boryl ketones by using a single copper catalyst. 24 Therefore, we are interested in whether the current reaction can also occur with only a copper catalyst. To confirm this, we performed the related DFT calculations.…”

“…Several attractive strategies have emerged for the borofunctionalization of unactivated alkenes to give β-boryl products. [18][19][20][21][22][23] In this regard, inspired by the seminal work of Brown and co-workers, 16 Wu and co-workers 23,24 have developed a series of transition metal-catalyzed fourcomponent borocarbonylative reactions for the synthesis of β-boronyl carbonyl compounds. Recently, they reported the first example of the Cu/Pd-catalyzed synthesis of boron carbonyl compounds through the four-component borocarbonylation of vinylarenes, aryl halides/triflates, B 2 pin 2 , and CO. 23 Scheme 1 shows their two representative reactions.…”