scholarly journals Allylic alcohols and amines by carbenoid eliminative cross-coupling using epoxides or aziridines

2021 ◽  
Vol 17 ◽  
pp. 2385-2389
Author(s):  
Matthew J Fleming ◽  
David M Hodgson

α-Lithiated terminal epoxides and N-(tert-butylsulfonyl)aziridines undergo eliminative cross-coupling with α-lithio ethers, to give convergent access to allylic alcohols and allylic amines, respectively. The process can be considered as proceeding by selective strain-relieving attack (ring-opening) of the lithiated three-membered heterocycle by the lithio ether and then selective β-elimination of lithium alkoxide.

2019 ◽  
Author(s):  
Ke-Yin Ye ◽  
Terry McCallum ◽  
Song Lin

Organic radicals are generally short-lived intermediates with exceptionally high reactivity. Strategically, achieving synthetically useful transformations mediated by organic radicals requires both efficient initiation and selective termination events. Here, we report a new catalytic strategy, namely bimetallic radical redox-relay, in the regio- and stereoselective rearrangement of epoxides to allylic alcohols. This approach exploits the rich redox chemistry of Ti and Co complexes and merges reductive epoxide ring opening (initiation) with hydrogen atom transfer (termination). Critically, upon effecting key bond-forming and -breaking events, Ti and Co catalysts undergo proton-transfer/electron-transfer with one another to achieve turnover, thus constituting a truly synergistic dual catalytic system.<br>


2021 ◽  
Author(s):  
Rajneesh Misra ◽  
Yogjivan Rout

A series of multi acceptor based push-pull derivatives BTD2–BTD5 were designed and synthesized via Pd-catalyzed Sonogashira cross-coupling reaction followed by [2+2] cycloaddition–electrocyclic ring-opening reaction in which benzothiadiazole (BTD, A1), naphthalimide...


2018 ◽  
Vol 20 (24) ◽  
pp. 8035-8038 ◽  
Author(s):  
Yu Zheng ◽  
Bei-Bei Yue ◽  
Kun Wei ◽  
Yu-Rong Yang

Author(s):  
Jian Cao ◽  
Ling Chen ◽  
Feng‐Na Sun ◽  
Yu‐Li Sun ◽  
Ke‐Zhi Jiang ◽  
...  
Keyword(s):  

ChemInform ◽  
2015 ◽  
Vol 46 (36) ◽  
pp. no-no
Author(s):  
Yong Li ◽  
Zhishi Ye ◽  
Tabitha M. Bellman ◽  
Teng Chi ◽  
Mingji Dai

Synlett ◽  
2020 ◽  
Author(s):  
Chuan Wang ◽  
Zhiyang Lin ◽  
Yun Lan

We report a reductive allylic defluorinative reaction of α-trifluoromethyl alkenes with terminal epoxides, which consists of an iodide-mediated regioselective ring opening and a nickel-catalyzed radical-type cross-coupling, providing diverse tertiary gem-difluorobishomoallylic alcohols in moderate to high yields. Notably, this reaction is conducted under mild conditions and requires no external ligand or proton donor.


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