One-Pot Formal Dehydrogenative Ketone Synthesis from Aldehydes and Non-activated Hydrocarbons

• Published in: Chemical & pharmaceutical bulletin Vol. 68; no. 4; pp. 336 - 338
• Main Authors: Yahata, Kenzo, Yoshioka, Shin, Hori, Shuhei, Sakurai, Shu, Kaneko, Yuki, Hasegawa, Kai, Akai, Shuji
• Format: Journal Article
• Language: English
• Published: TOKYO The Pharmaceutical Society of Japan 01.04.2020; Pharmaceutical Soc Japan; Japan Science and Technology Agency
• Subjects: Aldehydes; Aldehydes - chemistry; Chemical reactions; Chemical synthesis; Chemistry; Chemistry, Medicinal; Chemistry, Multidisciplinary; Coupling; Cycloalkanes; C–H activation; Dehydrogenation; Hydrocarbons; Hydrocarbons - chemistry; ketone synthesis; Ketones; Ketones - chemical synthesis; Ketones - chemistry; Life Sciences & Biomedicine; Molecular Structure; one-pot reaction; Oxidation; Pharmacology & Pharmacy; photo catalysis; Physical Sciences; Science & Technology; CONVERSION; ACYLATION; ALKYLATION; ketone synthesis; one-pot reaction; FLUORINATION; C(SP)-H FUNCTIONALIZATION; CATALYZED ELECTROSYNTHESIS; C-H activation; NICKEL; CARBON-MONOXIDE; DECATUNGSTATE; ORGANIC HALIDES; photo catalysis; C–H activation
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.c20-00075

Ketones are a fundamental functionality found throughout a range of natural and synthetic compounds, making their synthesis essential throughout the chemical disciplines. Herein, we describe a one-pot synthesis of ketones via decatungstate-mediated formal dehydrogenative coupling between aldehydes and non-activated hydrocarbons. A variety of substituted benzaldehydes and cycloalkanes could be used in the optimized reaction to produce the desired ketones in moderate yields. The decatungstate photocatalyst functions in two reactions in this synthesis, catalyzing both the coupling and oxidation steps of the process. Notably, the reaction displays both high atom economy and sustainability, as it uses light and oxygen as key energy sources.