1226953-82-7Relevant academic research and scientific papers
Synthesis of Secondary and Tertiary Alkyl Boronic Esters by gem-Carboborylation: Carbonyl Compounds as Bis(electrophile) Equivalents
Shi, Dunfa,Wang, Lu,Xia, Chungu,Liu, Chao
supporting information, p. 10318 - 10322 (2018/07/31)
An unprecedent gem-carboborylation of aldehydes and ketones provides access to various secondary and tertiary alkyl boronic esters. The addition of B2pin2 to a carbonyl compound generates α-oxyl-substituted alkyl boron species. Organ
Stereoselective formation of trisubstituted vinyl boronate esters by the acid-mediated elimination of α-hydroxyboronate esters
Guan, Weiye,Michael, Alicia K.,McIntosh, Melissa L.,Koren-Selfridge, Liza,Scott, John P.,Clark, Timothy B.
, p. 7199 - 7204 (2014/08/18)
The copper-catalyzed diboration of ketones followed by an acid-catalyzed elimination leads to the formation of 1,1-disubstituted and trisubstituted vinyl boronate esters with moderate to good yields and selectivity. Addition of tosic acid to the crude diboration products provides the corresponding vinyl boronate esters upon elimination. The trisubstituted vinyl boronate esters are formed as the (Z)-olefin isomer, which was established by subjecting the products to a Suzuki-Miyaura coupling reaction to obtain alkenes of known geometry.
Copper-catalyzed diboration of ketones: Facile synthesis of tertiary α-Hydroxyboronate esters
McIntosh, Melissa L.,Moore, Cameron M.,Clark, Timothy B.
supporting information; experimental part, p. 1996 - 1999 (2010/07/17)
Figure presented The diboration of ketones with the (ICy)CuOt-Bu catalyst was developed to provide access to tertiary α-hydroxyboronate esters. The (ICy)CuOt-Bu catalyst was generated in situ with (ICy)CuCl and NaOt-Bu to afford a more efficient catalyst than the preformed (ICy)CuOt-Bu. These conditions result in the diboration of various ketones in toluene at 50 °C in 2-22 h. Treatment of the resulting products with silica gel affords the corresponding α-hydroxyboronate esters.
