Platinum-Catalyzed Regio- and Stereoselective Diboration of Allenes by 1,8-Diaminonaphthalene-Protected Diboronic Acid (B 2 (dan) 2 )
Open Access
- 8 November 2025
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 90 (46) , 16568-16572
Abstract
We report a regio- and stereoselective diboration of the terminal C═C 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.Keywords
This publication has 26 references indexed in Scilit:
- Platinum-Catalyzed Diboration of Alkynes by 1,8-Diaminonaphthalene-Protected Diboronic Acid (B2(dan)2)The Journal of Organic Chemistry, 2024
- Copper-Catalyzed Borylation of Styrenes by 1,8-Diaminonaphthalene-Protected Diboronic AcidOrganic Letters, 2023
- Reactions of Diboron Reagents with Unsaturated Compounds2021
- Direct Synthesis of Multi(boronate) Esters from Alkenes and Alkynes via Hydroboration and Boration ReactionsACS Catalysis, 2020
- Stereoselective Syntheses of γ-Boryl Substitutedsyn-β-Alkoxy- andsyn-β-Amino-homoallylic Alcohols via a Regio- and Stereoselective Allene Diboration and Aldehyde Allylboration Reaction SequenceOrganic Letters, 2019
- Copper‐Catalyzed B(dan)‐Installing Allylic Borylation of Allylic PhosphatesAdvanced Synthesis & Catalysis, 2019
- Transition metal catalyzed element–element′ additions to alkynesCoordination Chemistry Reviews, 2017
- Diboron(4) Compounds: From Structural Curiosity to Synthetic WorkhorseChemical Reviews, 2016
- Recent developments in alkyne borylationsTetrahedron, 2014
- Platinum(0)-catalyzed diboration of allenes with bis(pinacolato)diboronTetrahedron Letters, 1998