Journal
ACS CATALYSIS
Volume 8, Issue 5, Pages 4622-4627Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.8b01224
Keywords
cross-coupling; hydrazone; phenol; alkyl nucleophile; nickel catalysis
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Funding
- Canada Research Chair Foundation
- Canadian Foundation for Innovation
- FRQNT Centre in Green Chemistry and Catalysis
- Natural Science and Engineering Research Council of Canada
- National Postdoctoral Program for Innovative Talents [BX201700110]
- China Postdoctoral Science Foundation [2017M623270]
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A nickel-catalyzed cross-coupling to construct the C(sp(2))-C(sp(3)) bond was developed from two sustainable biomass-based feedstocks: phenol derivatives with umpolung aldehydes. This strategy features the in situ generation of moisture/air-stable hydrazones from naturally abundant aldehydes, which act as alkyl nucleophiles under catalysis to couple with readily available phenol derivatives. The avoidance of using both halides as the electrophiles and organometallic or organoboron reagents (also derived from halides) as the nucleophiles makes this method more sustainable. Water tolerance, great functional group (ketone, ester, free amine, amide, etc.) compatibility, and late-stage elaboration of complex biological molecules exemplified its practicability and unique chemoselectivity over organometallic reagents.
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