PMID- 34807585
OWN - NLM
STAT- MEDLINE
DCOM- 20220228
LR  - 20221209
IS  - 1520-5126 (Electronic)
IS  - 0002-7863 (Print)
IS  - 0002-7863 (Linking)
VI  - 143
IP  - 48
DP  - 2021 Dec 8
TI  - Olefination via Cu-Mediated Dehydroacylation of Unstrained Ketones.
PG  - 20042-20048
LID - 10.1021/jacs.1c09587 [doi]
AB  - The dehydroacylation of ketones to olefins is realized under mild conditions, 
      which exhibits a unique reaction pathway involving aromatization-driven C-C 
      cleavage to remove the acyl moiety, followed by Cu-mediated oxidative elimination 
      to form an alkene between the alpha and beta carbons. The newly adopted 
      N'-methylpicolinohydrazonamide (MPHA) reagent is key to enable efficient cleavage 
      of ketone C-C bonds at room temperature. Diverse alkyl- and aryl-substituted 
      olefins, dienes, and special alkenes are generated with broad functional group 
      tolerance. Strategic applications of this method are also demonstrated.
FAU - Zhou, Xukai
AU  - Zhou X
AD  - Department of Chemistry, University of Chicago, Chicago, Illinois 60637, United 
      States.
FAU - Xu, Yan
AU  - Xu Y
AD  - Department of Chemistry, University of Chicago, Chicago, Illinois 60637, United 
      States.
FAU - Dong, Guangbin
AU  - Dong G
AUID- ORCID: 0000-0003-1331-6015
AD  - Department of Chemistry, University of Chicago, Chicago, Illinois 60637, United 
      States.
LA  - eng
GR  - R01 GM109054/GM/NIGMS NIH HHS/United States
PT  - Journal Article
PT  - Research Support, N.I.H., Extramural
PT  - Research Support, Non-U.S. Gov't
DEP - 20211122
PL  - United States
TA  - J Am Chem Soc
JT  - Journal of the American Chemical Society
JID - 7503056
RN  - 0 (Alkenes)
RN  - 0 (Hydrazones)
RN  - 0 (Indicators and Reagents)
RN  - 0 (Ketones)
RN  - 789U1901C5 (Copper)
SB  - IM
MH  - Acylation
MH  - Alkenes/*chemical synthesis
MH  - Catalysis
MH  - Copper/chemistry
MH  - Hydrazones/chemistry
MH  - Indicators and Reagents/chemistry
MH  - Ketones/*chemistry
PMC - PMC9116732
MID - NIHMS1802457
COIS- The authors declare no competing financial interests.
EDAT- 2021/11/23 06:00
MHDA- 2022/03/01 06:00
PMCR- 2022/12/08
CRDT- 2021/11/22 17:11
PHST- 2021/11/23 06:00 [pubmed]
PHST- 2022/03/01 06:00 [medline]
PHST- 2021/11/22 17:11 [entrez]
PHST- 2022/12/08 00:00 [pmc-release]
AID - 10.1021/jacs.1c09587 [doi]
PST - ppublish
SO  - J Am Chem Soc. 2021 Dec 8;143(48):20042-20048. doi: 10.1021/jacs.1c09587. Epub 
      2021 Nov 22.