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Fully automated flow protocol for C(sp3)–C(sp3) bond formation from tertiary amides and alkyl halides

Abstract:
Herein, we present a novel C(sp3)–C(sp3) bond-forming protocol via the reductive coupling of abundant tertiary amides with organozinc reagents prepared in situ from their corresponding alkyl halides. Using a multistep fully automated flow protocol, this reaction could be used for both library synthesis and target molecule synthesis on the gram-scale starting from bench-stable reagents. Additionally, excellent chemoselectivity and functional group tolerance make it ideal for late-stage diversification of druglike molecules.
Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1021/acs.orglett.3c01390

Authors


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Role:
Author
ORCID:
0000-0002-1302-7865
More by this author
Role:
Author
ORCID:
0000-0002-5632-1802


Publisher:
American Chemical Society
Journal:
Organic Letters More from this journal
Place of publication:
United States
Publication date:
2023-05-23
Acceptance date:
2023-05-18
DOI:
EISSN:
1523-7052
ISSN:
1523-7060
Pmid:
37219892


Language:
English
Keywords:
Pubs id:
1344585
Local pid:
pubs:1344585
Deposit date:
2023-10-03

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