ArticleChemical science2017
Selective uni- and bidirectional homologation of diborylmethane.
Article in Chemical science, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed.
- Enantioenriched Alkylboron Synthesis Via a Chiral Diborylalkane Platform.Journal of the American Chemical Society · 2026Article
- Converting 1,1-Bisborylalkanes into 1,2-Bisborylalkanes Enabled by Iron Ligand-to-Metal Charge Transfer (LMCT) Photocatalysis.Angewandte Chemie (International ed. in English) · 2026Article
- Site-Selective Activation and Stereospecific Functionalization of Bis(boronic Esters) Derived from 2-Alkenes: Construction of Propionates and Other 1,2-Difunctional Motifs.Angewandte Chemie (International ed. in English) · 2024Article
- Enantio- and Regioselective Cascade Hydroboration of Methylenecyclopropanes for Facile Access to Chiral 1,3- and 1,4-Bis(boronates).Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- 1,2-Metallate Rearrangement as a Toolbox for the Synthesis of Allylic Alcohols.The Journal of organic chemistry · 2023Article
- Selective, Transition Metal-free 1,2-Diboration of Alkyl Halides, Tosylates, and Alcohols.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Transition Metal Catalyst Free Synthesis of Olefins from Organoboron Derivatives.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Review
- Conformationally Controlled Linear and Helical Hydrocarbons Bearing Extended Side Chains.Journal of the American Chemical Society · 2021Article
- Article
- Synthesis of 1,3-Bis-(boryl)alkanes through Boronic Ester Induced Consecutive Double 1,2-Migration.Angewandte Chemie (International ed. in English) · 2020Article
- Electrophilic fluoroalkylthiolation induced diastereoselective and stereospecific 1,2-metalate migration of alkenylboronate complexes.Chemical science · 2020Article
- Desymmetrization of CChemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- 1,Journal of the American Chemical Society · 2020Article
- A modular and concise approach to MIDA acylboronatesChemical science · 2019Article
- A Boron Alkylidene-Alkene Cycloaddition Reaction: Application to the Synthesis of Aphanamal.Angewandte Chemie (International ed. in English) · 2017Article
- Enantioselective γ-borylation of unsaturated amides and stereoretentive Suzuki-Miyaura cross-coupling.Chemical science · 2017Article
Corrections and comments
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Authors and funding
6 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Diborylmethane can be homologated uni- and bidirectionally by using enantiomerically pure lithium-stabilized carbenoids to give 1,2- and 1,3-bis(boronic esters), respectively, in good yield and with excellent levels of enantio- and diastereoselectivity. The high sensitivity of the transformation to steric hindrance enables the exclusive operation of either manifold, effected through the judicious choice of the type of carbenoid, which can be a sparteine-ligated or a diamine-free lithiated benzoate/carbamate. The scope of the 1,2-bis(boronic esters) so generated is complementary to that encompassed by the asymmetric diboration of alkenes, in that primary-secondary and primary-tertiary 1,2-bis(boronic esters) can be prepared with equally high levels of selectivity and that functional groups, such as terminal alkynes and alkenes, are tolerated. Methods for forming
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.