Recent advances on transition-metal-catalyzed asymmetric tandem reactions with organoboron reagents

• Published in: Coordination chemistry reviews Vol. 392; pp. 35 - 48
• Main Authors: Yang, Xing, Kalita, Subarna Jyoti, Maheshuni, Srinivas, Huang, Yi-Yong
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 01.08.2019
• Subjects: Arylation; Boron reagent; Difunctionalization of alkene; Tandem reaction; Transition metal; Difunctionalization of alkene; Arylation; Transition metal; Boron reagent; Tandem reaction
• ISSN: 0010-8545; 1873-3840
• DOI: 10.1016/j.ccr.2019.04.009

This review mainly aims to highlight recent advances on this topic (2013–2019), along with introducing various types of two- and three-component reaction models, organoboron reagents and their reactive counterparts, as well as chiral organometallic catalysts. The inherent challenges, mechanistic insights and their applications toward natural products are also discussed. [Display omitted] •Tandem reactions involving several sequential CC or CX (X = B, F or N) bond formations in one operation.•Initial reactive intermediates obtained from the transmetalation of organoboron reagents.•Reactions ended with the reductive coupling reaction of organoboron reagents.•A single chiral transition-metal catalyst or cooperative dual chiral catalysts were applied.•Asymmetric difunctionalization of alkenes with aryl- and diboronate reagents. The in-depth research on merging organoboron reagents with unique characteristics and asymmetric tandem reaction strategy has inspired particular interest on account of the synthetic power for a wide array of chiral complicated molecules that may otherwise be difficult to obtain. Found on the well-established transition-metal-catalyzed Suzuki-Miyaura cross coupling reactions and asymmetric nucleophilic addition of CX (X = C, O or N) double bonds with organoboron reagents, single or dual chiral catalysts can enable generating reactive intermediates to initiate subsequent multiple CC or CY (Y = B, F, N or Sn) bond formations in one operation involving the use of organoboron reagents. This review mainly aims to highlight recent advances on transition-metal-catalyzed asymmetric tandem reactions with organoboron reagents (2013–2019), along with introducing various types of two- and three-component reaction models, organoboron reagents and their reactive counterparts, as well as chiral transition metal catalysts. The inherent challenges, mechanistic insights and synthetic applications toward natural products are also discussed.