Journal
ORGANIC LETTERS
Volume 16, Issue 9, Pages 2422-2425Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol500790p
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Funding
- European Community's ERC grant [227763]
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We report a general preparation of heteroarylmethylzinc chlorides by direct zinc insertion into heteroarylmethyl chlorides, along with a facile and straightforward synthesis of these heterocyclic chloromethyl precursors. We demonstrate that heteroarylmethylzinc reagents undergo various reactions including cross-couplings, allylations, acylations, and addition reactions to aldehydes, leading to polyfunctional heterocyclic products. Furthermore, these heteroaromatic zinc compounds prove to be versatile reagents for the preparation of various N- and O-heterocycles and give access to an analogue of a CB1 modifier.
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