249764-82-7

Upstream product

• 609-67-6 2-Iodobenzoyl chloride 
• 585-32-0 2-phenyl-2-propylamine 
• 98-88-4 benzoyl chloride 
• 617-94-7 1-methyl-1-phenylethyl alcohol 
• 32366-26-0 cumyl azide 
• 82573-53-3 N-(1-methyl-1-phenylethyl)benzamide 

Relevant academic research and scientific papers

Enantioselective synthesis of axially chiral biaryls by the pd-catalyzed suzuki-miyaura reaction: Substrate scope and quantum mechanical investigations

We report efficient syntheses of axially chiral biaryl amides in yields ranging from 80-92%, and with enantioselectivity in the range 88-94% ee employing an asymmetric Suzuki-Miyaura process with Pd(OAc)2 and KenPhos as ligand. These studies demonstrate that electron-rich and electron-deficient o-halobenzamides can be efficiently coupled with 2-methyl-1-naphthylboronic acid and 2-ethoxy-1-naphthylboronic acid. The yields and selectivities of the reactions are independent of the nature of halogen substituent on the benzamide coupling partner. Our investigations demonstrate that axially chiral heterocyclic and biphenyl compounds can also be synthesized with this methodology. We also report computational studies used to determine the origin of stereoselectivity during the selectivity-determining reductive elimination step of the related coupling of tolyl boronic acid with naphthylphosphonate bromide that was reported in a previous publication (J. Am. Chem. Soc. 2000, 122, 12051-12052). These studies indicate that the stereoselectivity arises from a combination of weak -(C)H??O interactions as well as steric interactions between the tolyl and naphthylphosphonate addends in the transition state for C-C coupling.

Ortho-directed functionalization of arenes using magnesate bases

Ortho-directed functionalisation of arenes using lithium alkylmagnesate bases were achieved, demonstrating the potential use of arylmagnesates as suitable arylanions, without a further transmetallation step, for challenging functionalizations such as fluorination, hydroxylation, arylation, vinylation and alkylation through epoxide ring-opening.

N-cumyl benzamide, sulfonamide, and aryl O-carbamate directed metalation groups. Mild hydrolytic lability for facile manipulation of directed ortho metalation derived aromatics

(Matrix Presented) N-Cumyl benzamide (2), sulfonamide (8), and O-carbamate (11) compounds undergo directed ortho metalation under standard conditions to give, after quench with a variety of electrophiles, the substituted products 3, 9, and 12, respectively. Regiospecific and convenient approaches to phthalimides (7), 1,2-benzisothiazole 1,1-dioxides (10b), and ortho-substituted phenols (13a) and salicylamides (13b) are thereby established The mild deprotection protocol for these new cumyl directed metalation groups (DMGs) suggests that they will supersede previous corresponding groups for synthetic anionic aromatic chemistry.