Selective uni- and bidirectional homologation of diborylmethane was written by Blair, Daniel J.;Tanini, Damiano;Bateman, Joseph M.;Scott, Helen K.;Myers, Eddie L.;Aggarwal, Varinder K.. And the article was included in Chemical Science in 2017.Electric Literature of C8H9FO This article mentions the following:
Diborylmethane can be homologated uni- and bidirectionally by using enantiomerically pure lithium-stabilized carbenoids to give 1,2- and 1,3-bis(boronic esters), resp., 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 asym. 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 C2-sym. and non-sym. anti and syn 1,3-bis(boronic esters) are also described and represent a powerful route towards 1,3-functionalized synthetic intermediates. In the experiment, the researchers used many compounds, for example, (S)-1-(2-Fluorophenyl)ethanol (cas: 171032-87-4Electric Literature of C8H9FO).
(S)-1-(2-Fluorophenyl)ethanol (cas: 171032-87-4) belongs to alcohols. Alcohols are weak acids. The most acidic simple alcohols (methanol and ethanol) are about as acidic as water, and most other alcohols are somewhat less acidic. Grignard and organolithium reagents are powerful tools for organic synthesis, and the most common products of their reactions are alcohols.Electric Literature of C8H9FO
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts