Concepedia

Stereospecific Nickel‐Catalyzed Cross‐Coupling Reactions of Alkyl Grignard Reagents and Identification of Selective Anti‐Breast‐Cancer Agents

Ivelina M. Yonova, A. George Johnson, Charlotte A. Osborne, Curtis E. Moore, Naomi S. Morrissette, Elizabeth R. Jarvo

Angewandte Chemie · 2014 · 47 citations · 38 references

DOI

Concepts

Abstract

Abstract Alkyl Grignard reagents that contain β‐hydrogen atoms were used in a stereospecific nickel‐catalyzed cross‐coupling reaction to form C(sp 3 )C(sp 3 ) bonds. Aryl Grignard reagents were also utilized to synthesize 1,1‐diarylalkanes. Several compounds synthesized by this method exhibited selective inhibition of proliferation of MCF‐7 breast cancer cells.

References

38

Enantioselective Addition of Organometallic Reagents to Carbonyl Compounds: Chirality Transfer, Multiplication, and Amplification

Ryōji Noyori, Masato Kitamura · Angewandte Chemie International Edition in English · 1991 · 1.2K citations

, , +13

Ligand Redox Effects in the Synthesis, Electronic Structure, and Reactivity of an Alkyl−Alkyl Cross-Coupling Catalyst

Gavin D. Jones, Jason Martin, Chris McFarland et al. · Journal of the American Chemical Society · 2006 · 478 citations

Cross Coupling Reactions of Chiral Secondary Organoboronic Esters With Retention of Configuration

Daisuke Imao, Ben W. Glasspoole, Véronique S. Laberge et al. · Journal of the American Chemical Society · 2009 · 366 citations

, , +13

Nickel-Catalyzed Cross Couplings of Benzylic Ammonium Salts and Boronic Acids: Stereospecific Formation of Diarylethanes via C–N Bond Activation

Prantik Maity, Danielle M. Shacklady‐McAtee, Glenn P. A. Yap et al. · Journal of the American Chemical Society · 2012 · 281 citations · Full text

, , +12

Nickel-Catalyzed Cross-Couplings of Benzylic Pivalates with Arylboroxines: Stereospecific Formation of Diarylalkanes and Triarylmethanes

Qi Zhou, Harathi D. Srinivas, Srimoyee Dasgupta et al. · Journal of the American Chemical Society · 2013 · 270 citations · Full text

, , +13