2011
DOI: 10.1002/ange.201107605
|View full text |Cite
|
Sign up to set email alerts
|

A Highly Efficient Gold‐Catalyzed Oxidative CC Coupling from CH Bonds Using Air as Oxidant

Abstract: „Tief Luftholen“ ist angesagt für die Titelreaktion, die Amine unter milden Bedingungen mit Nitroalkanen und nichtmodifizierten Ketonen kuppelt, denn dabei dient Luft alleine als Oxidationsmittel. Der praktische Prozess kommt mit geringen Katalysatormengen aus und liefert die Produkte nach kurzen Reaktionszeiten in guten Ausbeuten.

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

1
20
0
4

Year Published

2012
2012
2015
2015

Publication Types

Select...
9

Relationship

0
9

Authors

Journals

citations
Cited by 62 publications
(25 citation statements)
references
References 70 publications
(13 reference statements)
1
20
0
4
Order By: Relevance
“…Despite significant progress, the promising oxidative CÀH/CÀH cross-coupling reactions which obviate the prefunctionalization of both coupling partners have been largely under developed. To the best of our knowledge, only the gold-catalyzed oxidative C(sp 2 ) À H/ C(sp 2 ) À H homocoupling, [6] C(sp 3 ) À H/C(sp 3 ) À H [7] cross-coupling, and C(sp 2 )ÀH/C(sp)ÀH cross-coupling [5] have been realized, and the C(sp 3 )ÀH/C(sp)ÀH cross-coupling still remains unexplored. Following our work in C(sp 3 )ÀH functionalization, [8] we were interested in the gold-catalyzed direct C(sp 3 )ÀH alkynylation.…”
mentioning
confidence: 99%
“…Despite significant progress, the promising oxidative CÀH/CÀH cross-coupling reactions which obviate the prefunctionalization of both coupling partners have been largely under developed. To the best of our knowledge, only the gold-catalyzed oxidative C(sp 2 ) À H/ C(sp 2 ) À H homocoupling, [6] C(sp 3 ) À H/C(sp 3 ) À H [7] cross-coupling, and C(sp 2 )ÀH/C(sp)ÀH cross-coupling [5] have been realized, and the C(sp 3 )ÀH/C(sp)ÀH cross-coupling still remains unexplored. Following our work in C(sp 3 )ÀH functionalization, [8] we were interested in the gold-catalyzed direct C(sp 3 )ÀH alkynylation.…”
mentioning
confidence: 99%
“…However, the pre- 20 functionalization of the starting materials in this protocol limited its application. More recently, combination of selective, catalytic activation of C-H bonds with functionalization to form C-S bonds has been a subject of particular interest in recent years.Various catalytic systems based on copper, 11 palladium, 12-15 ruthenium [16][17][18][19][20][21][22][23][24][25] 19 and rhodium 17- …”
mentioning
confidence: 99%
“…

The direct oxidative cross-dehydrogenative coupling (CDC) of two C À H bonds can be an efficient and relatively clean strategy in organic synthesis. Among these reactions, the oxidation of tertiary amines to generate iminium intermediates, as pioneered by Murahashi et al, [7] Li et al [8] and others, [9][10][11] has received considerable attention. Among these reactions, the oxidation of tertiary amines to generate iminium intermediates, as pioneered by Murahashi et al, [7] Li et al [8] and others, [9][10][11] has received considerable attention.

…”
mentioning
confidence: 99%
“…The desired products were obtained with good enantioselectivity, but in lower yields ( Table 2, entries 9 and 10). [8][9][10][11] In summary, we have developed an enantioselective, direct, oxidative cross-dehydrogenative coupling reaction of tertiary amines with aldehydes. Prolonging the reaction time only slightly improved the reaction yields (largely as a result of the instability of 3 before reduction) and led to lower ee values because of product racemization (Table 2, entries 9-11).…”
mentioning
confidence: 99%