The functionalization of mono- and octahydrospherosilicate with vinylboranes and allylboranes via hydrosilylation reaction in the presence of a Karstedt’s platinum (0) catalyst is presented. This is the catalytic route to obtain a new class of silsesquioxanes containing boron atoms in their structure in high yields (> / 90%) and with satisfactory...
N,N′-chelate organoboron compounds have been successfully applied in bioimaging, organic light-emitting diodes (OLEDs), functional polymer, photocatalyst, electroluminescent (EL) devices, and other science and technology areas. However, the concise and efficient synthetic methods become more and more significant for material science, biomedical res...
Published in Angewandte Chemie (International ed. in English)
α-Haloboronates are useful organic synthons that can be converted to a diverse array of α-substituted alkyl borons. Methods to α-haloboronates are limiting and often suffer from harsh reaction conditions. Reported herein is a photochemical radical C-H halogenation of benzyl N-methyliminodiacetyl (MIDA) boronates. Fluorination, chlorination, and bro...
Published in Angewandte Chemie (International Ed. in English)
Configurationally stable and flexible organoboron helicenes consisting of either all‐ ortho ‐fused or a combination of angularly and linearly fused rings were synthesized by a modular approach from small achiral building blocks. A concept towards extended organoboron helices comprising both types of helically chiral compounds as primary substructur...
This work is focused on two areas: the chemistry of organofluorine and organoboron compounds. In the first chapter, a copper-catalysed synthesis of tri- and tetrasubstituted allenylboronic acids is presented. Extension of the same method leads to allenylboronic esters. The very reactive and moisture-sensitive allenylboronic acids are further applie...
Published in ACS Infectious Diseases
A series of benzimidazole–benzoxaborole hybrid molecules linked via an amide linker are described that exhibit good in vitro activity against Onchocerca volvulus , a filarial nematode responsible for the disease onchocerciasis, also known as river blindness. The lead identified in this series, 8a (AN8799), was found to have acceptable pharmacokine...
Published in ACS Infectious Diseases
The optimization of a series of benzimidazole–benzoxaborole hybrid molecules linked via a ketone that exhibit good activity against Onchocerca volvulus , a filarial nematode responsible for the disease onchocerciasis, also known as river blindness, is described. The lead identified in this series, 21 (AN15470), was found to have acceptable pharmaco...
Published in Synlett : accounts and rapid communications in synthetic organic chemistry
Previous work has demonstrated that variants of a heme protein, Rhodothermus marinus cytochrome c (Rma cyt c), catalyze abiological carbene boron-hydrogen (B-H) bond insertion with high efficiency and selectivity. Here we investigated this carbon-boron bondforming chemistry with cyclic, lactone-based carbenes. Using directed evolution, we obtained ...
Published in Angewandte Chemie (International ed. in English)
The enantiospecific coupling of secondary and tertiary boronic esters to aromatics has been investigated. Using p-lithiated phenylacetylenes and a range of boronic esters coupling has been achieved by the addition of N-bromosuccinimide (NBS). The alkyne functionality of the intermediate boronate complex reacts with NBS triggering the 1,2-migration ...
Published in Chemistry (Weinheim an der Bergstrasse, Germany)
The generation of in situ sp2 -sp3 diboron adducts has revolutionised the synthesis of organoboranes. Organocatalytic diboration reactions have represented a milestone in terms of unpredictable reactivity of these adducts. However, current methodologies have limitations in terms of substrate scope, selectivity and functional group tolerance. Here a...
