Deconstructive fluorination of cyclic amines by carbon-carbon cleavage

Science
Jose B RoqueRichmond Sarpong

Abstract

Deconstructive functionalizations involving scission of carbon-carbon double bonds are well established. In contrast, unstrained C(sp3)-C(sp3) bond cleavage and functionalization have less precedent. Here we report the use of deconstructive fluorination to access mono- and difluorinated amine derivatives by C(sp3)-C(sp3) bond cleavage in saturated nitrogen heterocycles such as piperidines and pyrrolidines. Silver-mediated ring-opening fluorination using Selectfluor highlights a strategy for cyclic amine functionalization and late-stage skeletal diversification, establishing cyclic amines as synthons for amino alkyl radicals and providing synthetic routes to valuable building blocks.

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Citations

Nov 2, 2018·Nature·Jose B RoqueRichmond Sarpong
May 28, 2019·Angewandte Chemie·Wu LiMatthias Beller
Dec 24, 2019·Angewandte Chemie·Jian-Wu ZhangBing Han
Jan 28, 2020·Angewandte Chemie·Brian WangRichmond Sarpong
Jan 7, 2021·Organic & Biomolecular Chemistry·Dayanne R Carvalho, Alec H Christian
Mar 24, 2021·Journal of the American Chemical Society·Yuegang ChenZhiwei Zuo
May 7, 2021·Organic Letters·Jianyou ZhaoZhong-Quan Liu
Jul 8, 2021·Journal of the American Chemical Society·Philipp SpießNuno Maulide
Jul 17, 2021·Nature Communications·Zhe ChangDepeng Zhao
Aug 11, 2021·Chemical Communications : Chem Comm·Shuai LiuLi-Na Guo
Aug 18, 2020·Journal of the American Chemical Society·Paul R LegerRichmond Sarpong
Sep 14, 2019·Journal of the American Chemical Society·Zhaofeng WangMarcos G Suero
Oct 24, 2018·Organic Letters·Ji-Shu ZhangLi-Biao Han
Oct 6, 2018·Journal of the American Chemical Society·Anhua HuZhiwei Zuo
Jul 7, 2021·Angewandte Chemie·Haitao QinHongjian Lu
Jul 7, 2020·Journal of the American Chemical Society·Jin Su HamRichmond Sarpong
Jul 7, 2020·Journal of the American Chemical Society·Jianbo Zhang, Sukbok Chang
Jun 17, 2020·The Journal of Organic Chemistry·Robert-Cristian RacleaPhilip J Parsons
Jun 28, 2019·Journal of the American Chemical Society·Kaining ZhangZhiwei Zuo
Oct 7, 2020·Organic Letters·Babasaheb Sopan GoreJeh-Jeng Wang
Sep 3, 2021·Chemistry : a European Journal·Luca DemontiNoel Nebra

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