Platinum-Catalyzed Regio- and Stereoselective Diboration of Allenes by 1,8-Diaminonaphthalene-Protected Diboronic Acid (B2(dan)2)
Yuki Ito, Tairin Kawasaki, Yusuke Yoshigoe, Shinichi Saito
TL;DR
A new platinum-catalyzed method for selectively adding boron atoms to allenes is developed, allowing for versatile chemical transformations.
Contribution
A regio- and stereoselective diboration method using Pt and B2(dan)2 is introduced for allene substrates.
Findings
The reaction works for various allenes, including 1-aryl and 1,1-disubstituted types.
The diboration products allow chemoselective transformations due to differing reactivities of the boryl groups.
Abstract
We report a regio- and stereoselective diboration of the terminal CC bond of allenes by B2(dan)2 (dan = naphthalene-1,8-diaminato) in the presence of a Pt catalyst. This reaction is applicable to a broad range of substrates, including 1-arylallenes and 1,1-disubstituted allenes. The two boryl groups in the product exhibit distinct reactivities, enabling chemoselective transformations.
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Taxonomy
TopicsOrganoboron and organosilicon chemistry · Catalytic C–H Functionalization Methods · Boron Compounds in Chemistry