Nickel(0)‐Catalyzed Hydroarylation of Styrenes and 1,3‐Dienes with Organoboron Compounds

• Published in: Angewandte Chemie International Edition Vol. 57; no. 2; pp. 461 - 464
• Main Authors: Xiao, Li‐Jun, Cheng, Lei, Feng, Wei‐Min, Li, Mao‐Lin, Xie, Jian‐Hua, Zhou, Qi‐Lin
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 08.01.2018; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: alkenes; Chemistry; Chemistry, Multidisciplinary; coupling reactions; Dienes; hydroarylation; Nickel; Nickel compounds; Organoboron compounds; organoboron reagents; Physical Sciences; Retinoic acid; Science & Technology; Styrenes; nickel; RAW-MATERIALS; coupling reactions; HYDROXYLATION; alkenes; MONOOXYGENASES; FATTY-ACID; CHEMISTRY; HYDROGEN-PEROXIDE; P450; hydroarylation; organoboron reagents; H2O2-DEPENDENT CYTOCHROME P450(SP-ALPHA); LACTATE OXIDASE; OXYFUNCTIONALIZATION REACTIONS
• ISSN: 1433-7851; 1521-3773; 1521-3773
• DOI: 10.1002/anie.201710735

A Ni‐catalyzed hydroarylation of styrenes and 1,3‐dienes with organoboron compounds has been developed. The reaction offers a highly selective approach to diarylalkanes and allylarenes under redox‐neutral conditions. In this hydroarylation reaction, a new strategy that uses the proton of methanol to generate the active catalyst species Ni−H was developed. The Ni‐catalyzed hydroarylation, combined with a Ir‐catalyzed C−H borylation, affords a very efficient and straightforward access to a retinoic acid receptor agonist. OH yeah: A nickel(0)‐catalyzed hydroarylation of alkenes with organoboron reagents using an alcohol OH group as the H‐atom source is reported. The reaction offers a highly selective approach to diarylalkanes and allylarenes under redox‐neutral conditions.