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Synlett 1990; 1990(3): 119-128
DOI: 10.1055/s-1990-21009
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The Evolution of Higher Order Cyanocuprates

Bruce H. Lipshutz*
  • *Department of Chemistry, University of California, Santa Barbara, CA 93106, USA
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Publication Date:
08 March 2002 (online)

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A personalized account of the rationales and events which led to the development of new synthetic methods based on cyanocuprate reagents is presented, highlighting the results from our laboratories over the last 10 years. 1. Introduction 2. Developing the Chemistry of R2Cu(CN)Li2 3. Second Generation Reagents: RtRrCu(CN)Li2 4. Mixed Metal Reagents: RtRrCu(CN)LiM, M ≠ Li 5. The Transmetalation Game 5.1. 1-Alkenylstannaties 5.2. Tin Hydrides → Stannylcuprates 5.3. Cul/Bu3SnH:Conjugate Reductions 5.4. Introduction of the Me3Sn Group 5.5. Transmetalations of Me3Sn-SiMe2R: Formation of Silylcuprates 5.6. The Allylic Cuprate Story 6. Prospects of the Future 7. Final Comments: Do Higher Order Cyanocuprates Really Exist?

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