Simple, High-Yield Methods for the Synthesis of Aldehydes Directly from o-, m-, and p-Carborane and Their Further Conversions

Abstract

Aldehydes have long served as important building blocks for synthetic chemists, and carboranyl aldehydes are no exception. Recent literature reports, for example, illustrate their application as intermediates in biomedicine, materials science, and basic organic chemistry. We report here new methods for the single-step preparation of C-monoformyl and C,C-diformyl derivatives directly from o-, m-, and p-carborane, as well as improved synthetic routes to homologated carboranyl aldehydes. Additionally, reductive amination is used to transform these aldehydes into a series of 2 degrees amines of alpha-amino acid esters.

Tuning the Optical Properties of 2‐Thienylpyridyl Iridium Complexes through Carboranes and Anions

“…(5)]. Therefore, we developed an effective synthetic method starting from C ‐formyl o ‐carborane26 and 4,4′‐dimethyl‐2,2′‐bipyridine [Scheme , Eq. (6)].…”

Synthesis of α-carboranyl-α-acyloxy-amides as potential BNCT agents

“…Lithiation of 1 with n -BuLi followed by the addition of methyl formate led to the formation of o -carborane aldehyde 2 8. Three component Passerini reaction of the aldehyde 2 with benzoic acid and benzyl isonitrile in water provided N -benzyl-α-carboranyl-α-benzoyloxy-acetamide 4 9.…”

Novel methodologies for the synthesis of functionalized lipophilic carboranes

“…We initiated the synthesis of the lipophilic carborane conjugates via the Baylis–Hillman reaction of hexadecyl acrylate 2 with carborane aldehyde6 1 in the presence of DABCO. The alcohol 3 thus obtained was treated with Ac 2 O in the presence of Mg(ClO 4 ) 2 to provide the acetate 4 7.…”