Abstract We disclose a protocol for the palladium‐catalyzed ortho ‐selective CH deuteration of arenes. Phenylacetic acids and benzoic are suitable substrates this reaction. This reaction offers catalytic route to ‐deuterated phenylacetic demonstrates sharp difference in reactivity palladacycle intermediates held together by weak strong coordination.

A protocol for the Pd(II)-catalyzed ortho-C–H alkylation of phenylacetic and benzoic acids using alkylboron reagents is disclosed. Monoprotected amino acid ligands (MPAA) were found to significantly promote reactivity. Both potassium alkyltrifluoroborates alkylboronic compatible coupling partners. The possibility a radical alkyl transfer Pd(II) was also investigated.

Selective incorporation of deuterium atoms into molecules is high interest for labeling purposes and optimizing properties drug candidates. A mild environmentally benign method the deuteration alkyl iodides via radical pathway using D2O as source has been developed. The reaction initiated mediated by triethylborane in presence dodecanethiol a catalyst. This compatible with wide range functional groups provides monodeuterated products good yields level incorporation. It opens promising...

The conversion of alkylboranes to the corresponding alkanes is classically per-formed via protonolysis alkylboranes. This simple reaction requires use severe conditions, that is, treatment with a carboxylic acid at high temperature (>150 °C). We report here mild radical procedure for transformation organoboranes alkanes. 4-tert-Butylcatechol, well-established inhibitor and antioxidant, acting as source hydrogen atoms. An efficient chain observed due exceptional reactivity phenoxyl radicals...

Mechanistic investigations on the previously reported reduction of B-alkylcatecholboranes in presence methanol led to disclosure a new mechanism involving catechol as reducing agent. More than just revising this reaction, we disclose here surprising role catechol, chain breaking antioxidant, which becomes source hydrogen atoms an efficient radical process.

Abstract When used with trialkylboranes, catechol derivatives, which are low‐cost and low toxicity, valuable hydrogen atom donors for radical chain reactions involving alkyl iodides related precursors. The system 4‐ tert ‐butylcatechol/triethylborane has been to reduce a series of secondary tertiary iodides, xanthate, thiohydroxamate ester. Catechol derivatives right in the optimal kinetic window synthetic applications, as demonstrated by highly efficient cyclizations. Cyclizations leading...

Abstract We disclose a protocol for the palladium‐catalyzed ortho ‐selective CH deuteration of arenes. Phenylacetic acids and benzoic are suitable substrates this reaction. This reaction offers catalytic route to ‐deuterated phenylacetic demonstrates sharp difference in reactivity palladacycle intermediates held together by weak strong coordination.

Abstract When used with trialkylboranes, catechol derivatives, which are low‐cost and low toxicity, valuable hydrogen atom donors for radical chain reactions involving alkyl iodides related precursors. The system 4‐ tert ‐butylcatechol/triethylborane has been to reduce a series of secondary tertiary iodides, xanthate, thiohydroxamate ester. Catechol derivatives right in the optimal kinetic window synthetic applications, as demonstrated by highly efficient cyclizations. Cyclizations leading...

Abstract A general strategy for the synthesis of aignopsanes, a new family sesquiterpene natural products marine origin, is presented. The total (+)‐aignopsanoic acid ( 1 ), (−)‐methyl aignopsanoate 2 and (−)‐isoaignopsanoic 3 ) has been achieved their absolute configuration confirmed. (+)‐Microcionin‐1 4 structurally related furanosesquiterpene isolated in both enantiomeric forms from sponges, was also synthesized its established an unambiguous way. Interestingly, we report that...

Abstract A protocol for the Pd(II)‐catalyzed ortho‐C—H alkylation of phenylacetic and benzoic acids using alkylboron reagents is disclosed.