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1.
J Org Chem ; 89(12): 9011-9018, 2024 Jun 21.
Article in English | MEDLINE | ID: mdl-38847456

ABSTRACT

C-O bond formation via C-H alkoxylation remains a challenge, especially coupling with a secondary alcohol, due to its low activity and sterically encumbered property. Here, we report a general and effective cobalt-catalyzed oxidative cross-coupling of benzamides with secondary alcohols via C-H alkoxylation reaction under solvothermal conditions, enabled by a salicylaldehyde/cobalt complex. The protocol features easy operation without additives, broad substrate scope, and excellent functional tolerance. The applicability is proven by the gram-scale synthesis and modification of natural products.

2.
J Org Chem ; 89(7): 4438-4443, 2024 Apr 05.
Article in English | MEDLINE | ID: mdl-38471105

ABSTRACT

A straight and efficient protocol for the synthesis of hindered indole-ethers via C-H alkoxylation of indoles was developed by a cobalt-catalyzed cross-dehydrogenative coupling reaction with secondary alcohols. The selection of the salicylaldehyde-Co(II) catalyst enables the reaction to proceed under conditions without acid or base addition in the presence of limited alcohols. The protocol has broad substrate scope for both indole and secondary alcohols and exhibits good functional tolerance. The synthetic applications are proven by gram-scale reaction and further diversification of the product. Preliminary mechanistic investigations indicate that the activation of C-H bonds is not the rate-determining step of the reaction.

3.
Chem Commun (Camb) ; 58(51): 7152-7155, 2022 Jun 23.
Article in English | MEDLINE | ID: mdl-35667557

ABSTRACT

We report a phosphine-directed ruthenium-catalyzed C8-selective alkylation of naphthalenes with alkenes. This protocol provides straightforward access to a large library of electron-rich C8-alkyl substituent 1-naphthphosphines, which outperformed common commercial phosphines and their precursors in the Pd-catalyzed Suzuki-Miyaura coupling of aryl bromides with alkylboronic acid.

4.
Org Lett ; 23(18): 7094-7099, 2021 09 17.
Article in English | MEDLINE | ID: mdl-34449224

ABSTRACT

A cobalt-catalyzed annulation of the C(sp2)-H/N-H bond of indoloamides with alkynes assisted by 8-aminoquinoline is reported for the synthesis of six-membered indololactams. The use of salicylaldehyde as the ligand is crucial for this transformation. The protocol has a broad scope for both alkynes and indoles. Preparing an active Co complex illustrates that salicylaldehyde plays a key role in the C-H activation step. The synthetic applications are proven by the gram-scale reaction and one-step construction of the multicyclic 5-HT3 receptor antagonist.


Subject(s)
Aldehydes/chemistry , Alkynes/chemistry , Aminoquinolines/chemistry , Indoles/chemistry , Serotonin 5-HT3 Receptor Agonists/chemical synthesis , Amides/chemistry , Catalysis , Cobalt/chemistry , Molecular Structure , Serotonin 5-HT3 Receptor Agonists/chemistry
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