2011
DOI: 10.1039/c1cc14297f
|View full text |Cite
|
Sign up to set email alerts
|

Potassium tert-butoxide mediated Heck-type cyclization/isomerization–benzofurans from organocatalytic radical cross-coupling reactions

Abstract: A transition metal-free Heck-type cyclization/isomerization reaction has been developed. Mediated by potassium tert-butoxide and phenanthroline a variety of benzofuran derivatives have been synthesized.

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
2
1
1

Citation Types

1
53
0

Year Published

2013
2013
2023
2023

Publication Types

Select...
8
1

Relationship

0
9

Authors

Journals

citations
Cited by 125 publications
(54 citation statements)
references
References 35 publications
1
53
0
Order By: Relevance
“…[44] There is a growing body of literature in which KOtBu plus associated ligands are capable of promoting transition metal-free cross-coupling reactions between arenes and aryl halides. [45][46][47][48][49][50][51][52][53][54][55][56][57] Computational [58,59] and empirical studies implicate radical intermediates and electron transfer processes. While the findings from these reports may, in part, be applicable to our work, the formation of cine substitution products in the title reaction necessitates that aryne intermediates be considered alongside.…”
mentioning
confidence: 99%
“…[44] There is a growing body of literature in which KOtBu plus associated ligands are capable of promoting transition metal-free cross-coupling reactions between arenes and aryl halides. [45][46][47][48][49][50][51][52][53][54][55][56][57] Computational [58,59] and empirical studies implicate radical intermediates and electron transfer processes. While the findings from these reports may, in part, be applicable to our work, the formation of cine substitution products in the title reaction necessitates that aryne intermediates be considered alongside.…”
mentioning
confidence: 99%
“…[32][33][34] The KO t Bu-mediated reduction of diaryl ethers and alkyl aryl ethers by NaH in this work maybe follow the similar SET mechanism as well. To verify this hypothesis, several preliminary experiments were conducted.…”
Section: Figurementioning
confidence: 69%
“…We were interested to find out whether its deuterated counterpart would behave analogously. To do so, substrate 25- Product 26-d 29 can arise directly by the Pierre mechanism, while 26-d 30 would either require deuterium atom abstraction from benzene-d 6 or could arise through the Pierre mechanism through reaction with KD, generated during the reaction (Scheme 6B); (for spectra and D-incorporation calculations, see Supporting Information). 29 We compared the outcome of this experiment with that of entry 4 in Table 4.…”
Section: Journal Of the American Chemical Societymentioning
confidence: 99%
“…31 In deuterated benzene, the conversion of 22-d 6 to electron donor 23-d 5 would require that a C−D bond be broken (Scheme 4, inset). But this step of BHAS reactions is routinely not the ratedetermining step, and so no isotope effect is likely to be seen in this step.…”
Section: Journal Of the American Chemical Societymentioning
confidence: 99%