Silver-Catalyzed Decarboxylative Chlorination of Aliphatic Carboxylic Acids

Wang, Zhentao; Zhu, Lin; Yin, Feng; Su, Zhiwei; Li, Zhaodong; Li, Chaozhong

doi:10.1021/ja210361z

Cited by 235 publications

(84 citation statements)

References 75 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A preliminary screening confirmed the ability of catalytic amounts of silver in combination with a stoichiometric amount of oxidant to promote a radical decarboxylation process4142. The substrates, combined in the presence of AgNO 3 and K 2 S 2 O 8 in acetonitrile for 10 h at 50 °C furnished the desired product ( 1a ) in 5% yield (Table 1, entry 1).…”

Section: Resultsmentioning

confidence: 80%

Expeditious diastereoselective synthesis of elaborated ketones via remote Csp3–H functionalization

et al. 2017

View full text Add to dashboard Cite

The quest for selective C–H functionalization reactions, able to provide new strategic opportunities for the rapid assembly of molecular complexity, represents a major focus of the chemical community. Examples of non-directed, remote Csp3–H activation to forge complex carbon frameworks remain scarce due to the kinetic stability and thus intrinsic challenge associated to the chemo-, regio- and stereoselective functionalization of aliphatic C–H bonds. Here we describe a radical-mediated, directing-group-free regioselective 1,5-hydrogen transfer of unactivated Csp3–H bonds followed by a second Csp2–H functionalization to produce, with exquisite stereoselectivity, a variety of elaborated fused ketones. This study demonstrates that aliphatic acids can be strategically harnessed as 1,2-diradical synthons and that secondary aliphatic C–H bonds can be engaged in stereoselective C–C bond-forming reactions, highlighting the potential of this protocol for target-oriented natural product and pharmaceutical synthesis.

show abstract

Section: Resultsmentioning

confidence: 80%

Expeditious diastereoselective synthesis of elaborated ketones via remote Csp3–H functionalization

et al. 2017

View full text Add to dashboard Cite

show abstract

“…558 By using a phen bound silver catalyst, this reaction was shown to proceed at room temperature to yield a series of secondary and tertiary alkyl chlorides in good to excellent yields.…”

Section: Cu- Ag- and Au-catalyzed Reactionsmentioning

confidence: 99%

Modern Transition-Metal-Catalyzed Carbon–Halogen Bond Formation

2016

View full text Add to dashboard Cite

The high utility of halogenated organic compounds has prompted the development of a vast number of transformations which install the carbon-halogen motif. Traditional routes to these building blocks have commonly involved multiple steps, harsh reaction conditions, and the use of stoichiometric and/or toxic reagents. In this regard, using transition metals to catalyze the synthesis of organohalides has become a mature field in itself, and applying these technologies has allowed for a decrease in the production of waste, higher levels of regio- and stereoselectivity, and the ability to produce enantioenriched target compounds. Furthermore, transition metals offer the distinct advantage of possessing a diverse spectrum of mechanistic possibilities which translate to the capability to apply new substrate classes and afford novel and difficult-to-access structures. This Review provides comprehensive coverage of modern transition metal-catalyzed syntheses of organohalides via a diverse array of mechanisms. Attention is given to the seminal stoichiometric organometallic studies which led to the corresponding catalytic processes being realized. By breaking this field down into the synthesis of aryl, vinyl, and alkyl halides, it becomes clear which methods have surfaced as most favored for each individual class. In general, a pronounced shift toward the use of C-H bonds as key functional groups, in addition to methods which proceed by catalytic, radical-based mechanisms has occurred. Although always evolving, this field appears to be heading in the direction of using starting materials with a significantly lower degree of prefunctionalization in addition to less expensive and abundant metal catalysts.

show abstract

“…The molecular formula is C 11 H 22 O 2 . The acid G has one more C than the alcohol H because it is degraded by one C in the Hunsdiecker reaction [7,8] …”

Section: Solutionmentioning

confidence: 99%

Designing Exercises to Determine the Structural Formula of Organic Compounds Based on the Experimental Data

Giac¹,

Thanh²,

Ninh³

et al. 2017

WJCE

View full text Add to dashboard Cite

This paper introduces the way to design exercises to determine the structural formula of organic compounds based on the experimental data. They are structure, physical properties, typical chemical properties, synthesis methods and application. From that the authors have built the scheme to design exercises. On that basis, the authors compiled some exercises which are used for teaching and learning organic chemistry in university and high school.

show abstract

Silver-Catalyzed Decarboxylative Chlorination of Aliphatic Carboxylic Acids

Cited by 235 publications

References 75 publications

Expeditious diastereoselective synthesis of elaborated ketones via remote Csp3–H functionalization

Expeditious diastereoselective synthesis of elaborated ketones via remote Csp3–H functionalization

Modern Transition-Metal-Catalyzed Carbon–Halogen Bond Formation

Designing Exercises to Determine the Structural Formula of Organic Compounds Based on the Experimental Data

Contact Info

Product

Resources

About