Base metal-catalyzed alcohol C–C couplings under hydrogen transfer conditions

• Published in: Tetrahedron letters 2018-03, Vol.59 (12), p.1073-1079
• Main Authors: Cai, Yuan, Li, Feng, Li, Yu-Qing, Zhang, Wu-Bin, Liu, Feng-Hua, Shi, Shi-Liang
• Format: Article
• Language: English
• Subjects: Base metal; C–C coupling; Dehydrogenation and hydrogenation; Hydrogen transfer
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2018.01.077

[Display omitted] •Base metal-catalyzed transfer hydrogenative (TH) alcohol C–C couplings are discussed.•TH alcohol C–C couplings are among most ideal methods to form upgraded alcohols.•TH alcohol C–C couplings are byproduct-free or produce water as the sole byproduct.•TH coupling reactions are atom-economical, step-economical and redox-economical.•TH coupling reactions are complementary to traditional carbonyl addition methods. Comparing to classical Grignard-type carbonyl additions, transfer hydrogenative C–C bond-forming reactions using alcohols as carbonyl precursors have shown remarkable advantages from the perspective of atom economy, step economy and redox economy. The significant drawbacks of conventional method, such as the use of multi-step reactions, the premetalated reagents, and stoichiometric oxidants and reductants, can be avoided by using hydrogen transfer processes. Moreover, the development of reactions employing earth-abundant and eco-friendly base metal as catalysts is an important objective in modern sustainable chemistry. In this review, we summarized recent advances in base metal-catalyzed C–C coupling of alcohols under hydrogen transfer conditions.