BIOMAT Database Logo BIOMAT Database Logo

Kinetic resolution of sulfur-stereogenic sulfoximines by Pd(ii)-MPAA catalyzed C-H arylation and olefination. 2021

Kallol Mukherjee, and Nicolas Grimblat, and Somratan Sau, and Koushik Ghosh, and Majji Shankar, and Vincent Gandon, and Akhila K Sahoo
School of Chemistry, University of Hyderabad Hyderabad 500046 India akhilchemistry12@gmail.com akssc@uohyd.ac.in.

A direct Pd(ii)-catalyzed kinetic resolution of heteroaryl-enabled sulfoximines through an ortho-C-H alkenylation/arylation of arenes has been developed. The coordination of the sulfoximine pyridyl-motif and the chiral amino acid MPAA ligand to the Pd(ii)-catalyst controls the enantio-discriminating C(aryl)-H activation. This method provides access to a wide range of enantiomerically enriched unreacted aryl-pyridyl-sulfoximine precursors and C(aryl)-H alkenylation/arylation products in good yields with high enantioselectivity (up to >99% ee), and selectivity factor up to >200. The coordination preference of the directing group, ligand effect, geometry constraints, and the transient six-membered concerted-metalation-deprotonation species dictate the stereoselectivity; DFT studies validate this hypothesis.

UI MeSH Term Description Entries

Related Publications

Kallol Mukherjee, and Nicolas Grimblat, and Somratan Sau, and Koushik Ghosh, and Majji Shankar, and Vincent Gandon, and Akhila K Sahoo
Efficient Kinetic Resolution of Sulfur-Stereogenic Sulfoximines by Exploiting CpX RhIII -Catalyzed C-H Functionalization.
June 2019, Angewandte Chemie (International ed. in English),
Kallol Mukherjee, and Nicolas Grimblat, and Somratan Sau, and Koushik Ghosh, and Majji Shankar, and Vincent Gandon, and Akhila K Sahoo
Pd(II)-Catalyzed enantioselective C-H olefination toward the synthesis of P-stereogenic phosphinamides.
February 2024, Chemical communications (Cambridge, England),
Kallol Mukherjee, and Nicolas Grimblat, and Somratan Sau, and Koushik Ghosh, and Majji Shankar, and Vincent Gandon, and Akhila K Sahoo
Pd(II)-catalyzed enantioselective synthesis of P-stereogenic phosphinamides via desymmetric C-H arylation.
January 2015, Journal of the American Chemical Society,
Kallol Mukherjee, and Nicolas Grimblat, and Somratan Sau, and Koushik Ghosh, and Majji Shankar, and Vincent Gandon, and Akhila K Sahoo
Efficient Synthesis of Sulfur-Stereogenic Sulfoximines via Ru(II)-Catalyzed Enantioselective C-H Functionalization Enabled by Chiral Carboxylic Acid.
May 2021, Journal of the American Chemical Society,
Kallol Mukherjee, and Nicolas Grimblat, and Somratan Sau, and Koushik Ghosh, and Majji Shankar, and Vincent Gandon, and Akhila K Sahoo
Pd(II)-catalyzed olefination of sp3 C-H bonds.
March 2010, Journal of the American Chemical Society,
Kallol Mukherjee, and Nicolas Grimblat, and Somratan Sau, and Koushik Ghosh, and Majji Shankar, and Vincent Gandon, and Akhila K Sahoo
Pd(II)-catalyzed meta-C-H olefination, arylation, and acetoxylation of indolines using a U-shaped template.
July 2014, Journal of the American Chemical Society,
Kallol Mukherjee, and Nicolas Grimblat, and Somratan Sau, and Koushik Ghosh, and Majji Shankar, and Vincent Gandon, and Akhila K Sahoo
Pd(II)-catalyzed enantioselective C-H olefination of diphenylacetic acids.
January 2010, Journal of the American Chemical Society,
Kallol Mukherjee, and Nicolas Grimblat, and Somratan Sau, and Koushik Ghosh, and Majji Shankar, and Vincent Gandon, and Akhila K Sahoo
Pd(II)-catalyzed ortho- or meta-C-H olefination of phenol derivatives.
May 2013, Journal of the American Chemical Society,
Kallol Mukherjee, and Nicolas Grimblat, and Somratan Sau, and Koushik Ghosh, and Majji Shankar, and Vincent Gandon, and Akhila K Sahoo
Pd-Catalyzed Denitrative Intramolecular C-H Arylation.
June 2019, Organic letters,
Kallol Mukherjee, and Nicolas Grimblat, and Somratan Sau, and Koushik Ghosh, and Majji Shankar, and Vincent Gandon, and Akhila K Sahoo
Pd(II)-catalyzed para-selective C-H arylation of monosubstituted arenes.
September 2011, Journal of the American Chemical Society,
Copied contents to your clipboard!