A Coupling of Benzamides and Donor/Acceptor Diazo Compounds To Form γ-Lactams via Rh(III)-Catalyzed C–H Activation

Hyster, Todd K.; Ruhl, Kyle E.; Rovis, Tomislav

doi:10.1021/ja402274g

Cited by 479 publications

(151 citation statements)

References 47 publications

Supporting

Mentioning

135

Contrasting

Unclassified

Order By: Relevance

“…When 1e was and 1k were reacted at the same time,t he reaction favored the electron-deficient Nnitrosoaniline in a1 .33:1 ratio (Scheme 5b), thus implying that the CÀHa ctivation probably occurs by ac oncerted metalation-deprotonation (CMD) mechanism. [14] Moreover, an otable primary kinetic isotope effect was observed (K H / K D = 4.0), thus suggesting that C À Hbond cleavage should be involved in the rate-limiting step (Scheme 5c).…”

mentioning

confidence: 99%

Cationic Cobalt(III) Catalyzed Indole Synthesis: The Regioselective Intermolecular Cyclization of N‐Nitrosoanilines and Alkynes

2016

View full text Add to dashboard Cite

The unique regioselectivity and reactivity of cobalt(III) in the direct cyclization of N-nitrosoanilines with alkynes for the expedient synthesis of N-substituted indoles is demonstrated. In the presence of a cobalt(III) catalyst, high regioselectivity was observed when using unsymmetrical meta-substituted N-nitrosoanilines. Moreover, internal alkynes bearing electron-deficient groups, which are almost unreactive in the [Cp*Rh(III)]-catalyzed system, display good reactivity in this transformation.

show abstract

mentioning

confidence: 99%

Cationic Cobalt(III) Catalyzed Indole Synthesis: The Regioselective Intermolecular Cyclization of N‐Nitrosoanilines and Alkynes

2016

View full text Add to dashboard Cite

show abstract

“…[65] Gratifyingly, a range of γ-lactams could be formed using this method. The mechanism features the generation of a rhodium carbenoid, which can undergo 1,1-migratory insertion to form the six-membered rhodacyclic intermediate.…”

Section: Rhodium Catalysismentioning

confidence: 99%

A Simple and Versatile Amide Directing Group for C−H Functionalizations

et al. 2016

View full text Add to dashboard Cite

Achieving selective C–H activation at a single and strategic site in the presence of multiple C–H bonds can provide a powerful and generally useful retrosynthetic disconnection. In this context, the directing group serves as a compass to guide the transition metal to C–H bonds using distance and geometry as powerful recognition parameters to distinguish between proximal and distal C–H bonds. However, the installation and removal of directing groups is a practical drawback. To improve the utility of this approach, one can seek solutions in three directions. First, simplifying the directing group; Second, use of common functional groups or protecting groups as directing groups; Third, attaching the directing group to substrates via a transient covalent bond to render directing groups catalytic. This review describes the rational development of an extremely simple and yet broadly applicable directing group for Pd(II), Rh(III) and Ru(II) catalysts, namely, the N-methoxy amide (CONHOMe). Through collective efforts in the community, a wide range of C–H activation transformations using this type of simple directing groups has been developed.

show abstract

“…Recently, diazo compounds have been widely employed as a class of versatile alkylation reagents in metal catalyzed C-H alkylation [26][27][28][29]. In 2010, Yu reported a highly regioselective approach for C2 alkylation of free (N-H)-indoles and aryldiazoesters catalyzed by Ruthenium catalyst [30].…”

Section: Introductionmentioning

confidence: 99%

Rh(III)-Catalyzed, Highly Selectively Direct C–H Alkylation of Indoles with Diazo Compounds

Wan

Xing

et al. 2016

Catalysts

View full text Add to dashboard Cite

show abstract

A Coupling of Benzamides and Donor/Acceptor Diazo Compounds To Form γ-Lactams via Rh(III)-Catalyzed C–H Activation

Cited by 479 publications

References 47 publications

Cationic Cobalt(III) Catalyzed Indole Synthesis: The Regioselective Intermolecular Cyclization of N‐Nitrosoanilines and Alkynes

Cationic Cobalt(III) Catalyzed Indole Synthesis: The Regioselective Intermolecular Cyclization of N‐Nitrosoanilines and Alkynes

A Simple and Versatile Amide Directing Group for C−H Functionalizations

Rh(III)-Catalyzed, Highly Selectively Direct C–H Alkylation of Indoles with Diazo Compounds

Contact Info

Product

Resources

About