2019
DOI: 10.1039/c9ra06963a
|View full text |Cite
|
Sign up to set email alerts
|

Co-catalyzed ortho-C–H functionalization/annulation of arenes and alkenes with alkynylsilanes: access to isoquinolone and pyridone motifs

Abstract: A method for cobalt-catalyzed ortho-C–H functionalization annulation of arenes and alkenes with alkynylsilanes assisted by 8-aminoquinolyl auxiliary.

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
2
1
1
1

Citation Types

0
7
0

Year Published

2020
2020
2024
2024

Publication Types

Select...
4
3

Relationship

0
7

Authors

Journals

citations
Cited by 29 publications
(7 citation statements)
references
References 79 publications
0
7
0
Order By: Relevance
“…In the presence of NaOPiv•H 2 O, Co(OAc) 2 •4H 2 O/Ag 2 O-catalyzed decarboxylative C-H/N-H activation/annulation of N-PyO benzamides with alkynyl carboxylic acids under air in TFE also affords 3-substituted isoquinolones with high regioselectivity [67]. Similarly, 3-substituted isoquinolones can be obtained using Co(OAc) 2 •4H 2 O as catalyst from the reactions of N-(quinolin-8-yl)benzamides with alkynylsilanes with desilylation under oxygen in the same solvent, with the use of Mn(acac) 2 and CsF [68].…”
Section: Scheme 15 N-methoxy Isoquinolone Formation Via Highly Chemoselective N-h Activationmentioning
confidence: 99%
“…In the presence of NaOPiv•H 2 O, Co(OAc) 2 •4H 2 O/Ag 2 O-catalyzed decarboxylative C-H/N-H activation/annulation of N-PyO benzamides with alkynyl carboxylic acids under air in TFE also affords 3-substituted isoquinolones with high regioselectivity [67]. Similarly, 3-substituted isoquinolones can be obtained using Co(OAc) 2 •4H 2 O as catalyst from the reactions of N-(quinolin-8-yl)benzamides with alkynylsilanes with desilylation under oxygen in the same solvent, with the use of Mn(acac) 2 and CsF [68].…”
Section: Scheme 15 N-methoxy Isoquinolone Formation Via Highly Chemoselective N-h Activationmentioning
confidence: 99%
“…Recently, Lin and Shen introduced alkynylsilanes 104 as substrate to provide pyridones 89g-h. 102 Following their work on the cobalt-catalyzed C-H functionalization / cyclization of acrylamides 1s with alkynes, Daugulis' group reported an expansion of the scope to alkenes to afford dihydroisoquinolinones and dihydropyrid-2-ones 89i (Scheme 32). 103 The procedure was slightly modified by swapping the catalyst from Co(OAc)2 (10 mol%) to Co(acac)2 (20…”
Section: Cobalt Catalyzed Functionalization / Annulation Cascadementioning
confidence: 99%
“…Recently, Lin and Shen introduced alkynylsilane 104 as a substrate to provide pyridones 89g,h. 102 Their initial catalyst system consisted of Co(OAc) 2 •4H 2 O (20 mol%) with Mn(OAc) 2 as a co-oxidant, and required CsF (1.2 equiv) as a silaphilic base to remove silicon. Trimethylsilyl phenylacetylene 104 was used as a benchmark alkyne and coupling with several -and/or -substituted acrylamides was successfully achieved in trifluoroethanol at 100 °C under an oxygen atmosphere (Scheme 31, Conditions A), affording pyridones 89g in moderate to excellent yields.…”
Section: Scheme 31 Co-catalyzed Alkenylation/cyclization Of Acrylamidesmentioning
confidence: 99%
“…The present protocol was realized using benzamides 106 with alkynylsilanes 107 affording the corresponding isoquinolones 108 (Scheme 59). [87] Recently, Liu et al established Cp*-free cobaltcatalyzed CÀ H activation/annulation reaction using 2-(hydroxymethyl)pyridine as the traceless directing group (Scheme 60). [88]…”
Section: Co-catalyzed Isoquinoline Synthesismentioning
confidence: 99%
“…The present protocol was realized using benzamides 106 with alkynylsilanes 107 affording the corresponding isoquinolones 108 (Scheme 59). [87] …”
Section: Synthesis Of Isoquinoline Derivativesmentioning
confidence: 99%