A Convenient Synthesis of <i>N</i>‐Aryl Benzamides by Rhodium‐Catalyzed <i>ortho</i>‐Amidation and Decarboxylation of Benzoic Acids

Shi, Xiao‐Xin; Liu, Keyan; Fan, Juan; Dong, Xue‐Fen; Wei, Junfa; Li, Chao‐Jun

doi:10.1002/chem.201406031

Cited by 71 publications

(20 citation statements)

References 128 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…117 Notably, this strategy demonstrates the synthetic utility of a removable carboxylic acid directing group that both initiates Rh(III)-catalyzed ortho C–H aminocarbonylation and subsequently undergoes decarboxylative cleavage. Out of a variety of alkali phosphonate salts that were examined, K 2 HPO 4 was identified to be optimal, and in the absence of this additive none of the desired product was obtained.…”

Section: Isocyanatesmentioning

confidence: 95%

Transition-Metal-Catalyzed C–H Bond Addition to Carbonyls, Imines, and Related Polarized π Bonds

2016

View full text Add to dashboard Cite

The transition metal-catalyzed addition of C–H bonds to carbonyls, imines and related polarized π-bonds has emerged as a particularly efficient and powerful approach for the construction of an incredibly diverse array of heteroatom substituted products. Readily available and stable inputs are typically employed, and reactions often proceed with very high functionality group compatibility and without the production of waste byproducts. Additionally, many transition metal-catalyzed C–H bond additions to polarized π-bonds occur within cascade reaction sequences to provide rapid access to a diverse array of different heterocyclic as well as carbocyclic products. This review highlights the diversity of transformations that have been achieved, catalysts that have been used, and types of products that have been prepared through the transition metal catalyzed addition of C–H bonds to carbonyls, imines and related polarized π-bonds.

show abstract

Section: Isocyanatesmentioning

confidence: 95%

Transition-Metal-Catalyzed C–H Bond Addition to Carbonyls, Imines, and Related Polarized π Bonds

2016

View full text Add to dashboard Cite

show abstract

“…[30] It is worth noting that, contrary to when employing the Rh(III) catalyst, 2-methoxybenzoic acid was found to be compatible in this catalytic system and provided the desired products in 33% yield. [31] During the course of our investigation on the cyclization of otoluic acid with phenylisocyanate, 3-methyl-N- Isolated yields.…”

Section: Synthesis Of N-substituted Phthalimides Via Tandem 12-additmentioning

confidence: 99%

“…The substrate scope is similar to the Rhcatalyzed reaction (Table 4). [31] Scheme 11. Conjugate addition of 2-phenylpyridine analogues to a,b-unsaturated carbonyl compounds.…”

Section: P E R S O N a L A C C O U N T T H E C H E M I C A L R E C O R Dmentioning

confidence: 99%

Transition-Metal-Catalyzed Direct Addition of Aryl C-H Bonds to Unsaturated Electrophiles

Shi¹,

Han²,

Li³

2016

The Chemical Record

Self Cite

View full text Add to dashboard Cite

The direct addition of Csp(2) -H bonds onto polar C=C, C=O, and C=N bonds is both synthetically and mechanistically important, because using aromatic C-H substrates in place of organometallic reagents provides a more direct and atom-economical alternative to many important compounds without the pre-generation of organometallic compounds from stoichiometric halides and the unavoidable generation of stoichiometric metal halide waste. In this account, we summarize our contributions to the transition-metal-catalyzed addition of aromatic C-H bonds to polar C=C, C=O, and C=N bonds via directing-group-assisted regiospecific reactions. These synthetic methods provide efficient access to benzylic alcohols, alkylbenzenes, 3-substituted phthalides, N-substituted phthalimides, N-aryl benzamides, and indene derivatives from commercially available reagents. It is worth noting that valuable heterocycles such as 3-substituted phthalides and N-substituted phthalimides can be obtained in one step by this approach.

show abstract

“…53 This method uses catalytic amounts of Cu 2 O to promote protodecarboxylation of the amidation product. However, the authors showed that in its absence the desired decarboxylated product is obtained and although lower yields were exhibited, this showed the ability of rhodium to promote protodecarboxylation.…”

mentioning

confidence: 99%

The use of carboxylic acids as traceless directing groups for regioselective C–H bond functionalisation

et al. 2017

View full text Add to dashboard Cite

show abstract

A Convenient Synthesis of N‐Aryl Benzamides by Rhodium‐Catalyzed ortho‐Amidation and Decarboxylation of Benzoic Acids

Cited by 71 publications

References 128 publications

Transition-Metal-Catalyzed C–H Bond Addition to Carbonyls, Imines, and Related Polarized π Bonds

Transition-Metal-Catalyzed C–H Bond Addition to Carbonyls, Imines, and Related Polarized π Bonds

Transition-Metal-Catalyzed Direct Addition of Aryl C-H Bonds to Unsaturated Electrophiles

The use of carboxylic acids as traceless directing groups for regioselective C–H bond functionalisation

Contact Info

Product

Resources

About