Abstract
Planar chiral ferrocenes have received great attention in both academia and industry. Although remarkable progresses have been made over the past decade, the development of efficient and straightforward methods for the synthesis of enantiopure planar chiral ferrocenes remains highly challenging. Herein, we report a rhodium(I)/phosphonite catalyzed thioketone-directed enantioselective C-H bond arylation of ferrocenes. Readily available aryl iodides are used as the coupling partners in this transformation, leading to a series of planar chiral ferrocenes in good yields and excellent enantioselectivities (up to 86% yield, 99% ee). Of particular note, heteroaryl coupled ferrocenes, which are difficult to access with previous approaches, can be obtained in satisfactory results.
Highlights
Planar chiral ferrocenes have received great attention in both academia and industry
Glorius and coworkers have made breakthroughs that the combination of a rhodium(I) precatalyst with chiral N-heterocyclic carbene (NHC) or monodentate phosphonite ligand enabled highly enantioselective Csp3–H arylations[68,69]. Inspired by these pioneering results, we explore Rh(I) catalyzed enantioselective arylation of thiocarbonylferrocenes (Fig. 1b) after achieving the synthesis of axially chiral heterobiaryls via isoquinoline directed C-H functionalization[70]
In the presence of Rh (I) catalyst derived from a chiral phosphonite, direct arylation of thioketone substituted ferrocenes with readily available aryl iodides proceeds in excellent enantioselectivity
Summary
Planar chiral ferrocenes have received great attention in both academia and industry. The development of enantioselective C–H arylation reaction to provide structurally diverse planar chiral ferrocenes is highly desirable[42,43,44,45,46,47,48,49,50,51,52,53,54,55,56,57,58,59,60,61]. In the presence of Rh (I) catalyst derived from a chiral phosphonite, direct arylation of thioketone substituted ferrocenes with readily available aryl iodides proceeds in excellent enantioselectivity.
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