Dehydroxylative Cyanation of Alcohols Promoted by Triphenyphosphine/1,2-Diiodoethane

Article Chemistry, Multidisciplinary

Two-Stage Syntheses of Clionastatins A and B

Hao Cui et al.

Summary: A concise and divergent synthesis of the polychlorinated marine steroids clionastatin A and B has been achieved from inexpensive testosterone through a unique two-stage chlorination-oxidation strategy. Key features of the synthesis include highly selective chlorination reactions, photochemical reactions, and transposition reactions.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

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Article Chemistry, Physical

Nickel-Catalyzed Regiodivergent Cyanation of Allylic Alcohols: Scope, Mechanism, and Application to the Synthesis of 1,n-Dinitriles

Jinguo Long et al.

Summary: A regiodivergent cyanation of allylic alcohols under nickel catalysis was reported in this study, leading to the successful synthesis of challenging branched products. Dinitriles can also be obtained in good yields with high selectivity through subsequent hydrocyanation, which can be further functionalized into various compounds. Density functional theory (DFT) calculations provided insights into the role of ligands in tuning regioselectivity and reactivity.

ACS CATALYSIS (2021)

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Article Chemistry, Organic

Nickel-Catalyzed Isomerization/Allylic Cyanation of Alkenyl Alcohols

Ying Ding et al.

Summary: A nickel-catalyzed isomerization/allylic cyanation of alkenyl alcohols is reported, providing a new complement to allylic substitution reactions. The use of a specific diphosphite ligand and methanol as the solvent is crucial for the success of this transformation, as demonstrated by a gram-scale regioconvergent experiment and formal synthesis of quebrachamine showcasing the high potential of this methodology.

ORGANIC LETTERS (2021)

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Review Pharmacology & Pharmacy