Abstract
The development of environmentally benign, inexpensive, and earth-abundant metal catalysts is desirable from both an ecological and economic standpoint. Certainly, in the past couple decades, iron has become a key player in the development of sustainable coupling chemistry and has become an indispensable tool in organic synthesis. Over the last ten years, organic chemistry has witnessed substantial improvements in efficient synthesis because of domino reactions. These protocols are more atom-economic, produce less waste, and demand less time compared to a classical stepwise reaction. Although iron-catalyzed domino reactions require a mindset that differs from the more routine noble-metal, homogenous iron catalysis they bear the chance to enable coupling reactions that rival that of noble-metal-catalysis. This review provides an overview of iron-catalyzed domino coupling reactions of π-systems. The classifications and reactivity paradigms examined should assist readers and provide guidance for the design of novel domino reactions.
Highlights
Over the past couple decades, the use of transition-metal-catalyzed cross-coupling reactions have become a staple within the organic chemist’s arsenal of carbon–carbon and carbon–heteroatom bond-forming reactions
This review summarized Fe-catalyzed domino coupling reactions of π-systems and illustrated the major breakthroughs in the field
Considerable developments have been accomplished in the field of iron catalysis providing non-toxic, inexpensive, and overall greener alternatives to precious metal catalysis
Summary
Over the past couple decades, the use of transition-metal-catalyzed cross-coupling reactions have become a staple within the organic chemist’s arsenal of carbon–carbon and carbon–heteroatom bond-forming reactions. In 2015, Kang and co-workers described a FeCl2-catalyzed tandem cyclization/cross-coupling reaction of alkyl iodides 1 with aryl Grignard reagents 2 to give arylmethyl-substituted pyrrolidines and tetrahydrofurans 3 in poor to excellent yield (Scheme 3) [54]. Scheme 3: Iron-catalyzed tandem cyclization and cross-coupling reactions of iodoalkanes 1 with aryl Grignard reagents 2.
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