Rh(III)-catalyzed C-H activation of benzamides: Coupling with quinones

Article abstract of DOI:10.1016/S1872-2067(14)60245-X

Rh(III)-catalyzed C-H activation of N-(alkyl)benzamides in the oxidative coupling with various quinones. In addition, under redox-neutral conditions, 2-hydroxy-6H-benzo[c]chromen-6-ones were also obtained via a cascade of cross-coupling followed by lactonization.

Full text of DOI:10.1016/S1872-2067(14)60245-X

ChineseꢀJournalꢀofꢀCatalysisꢀ36ꢀ(2015)ꢀ48–56
ꢀ
ꢀ ꢀ ꢀ
ꢀ ꢀ ꢀ ꢀ
ava i l a b l e a t w w w. s c i e n c ed i r e c t . c o m
ꢀ
j o u r n a l h o m e p a g e : w w w. e l s e v i e r. c o m / l o c a t e /c h n j c
ꢀ
ꢀ
Article (Special Issue on Catalysis in Organic Synthesis)
Rh(III)‐catalyzedꢀC–Hꢀactivationꢀofꢀbenzamides:ꢀCouplingꢀwithꢀ
quinonesꢀ
ZisongꢀQi,ꢀXingweiꢀLiꢀ*
ꢀ
DalianꢀInstituteꢀofꢀChemicalꢀPhysics,ꢀChineseꢀAcademyꢀofꢀSciences,ꢀDalianꢀ116023,ꢀLiaoning,ꢀChinaꢀ ꢀ
A R T I C L E ꢀ I N F O ꢀ
A B S T R A C T ꢀ
Articleꢀhistory:ꢀ
Rh(III)‐catalyzedꢀ C–Hꢀ activationꢀ ofꢀ N‐(alkyl)benzamidesꢀ inꢀ theꢀ oxidativeꢀ couplingꢀ withꢀ variousꢀ
quinones.ꢀ Inꢀ addition,ꢀ underꢀ redox‐neutralꢀ conditions,ꢀ 2‐hydroxy‐6H‐benzo[c]chromen‐6‐onesꢀ
wereꢀalsoꢀobtainedꢀviaꢀaꢀcascadeꢀofꢀcross‐couplingꢀfollowedꢀbyꢀlactonization.ꢀ
©ꢀ2015,ꢀDalianꢀInstituteꢀofꢀChemicalꢀPhysics,ꢀChineseꢀAcademyꢀofꢀSciences.
PublishedꢀbyꢀElsevierꢀB.V.ꢀAllꢀrightsꢀreserved.
Receivedꢀ25ꢀSeptemberꢀ2014ꢀ
Acceptedꢀ10ꢀNovemberꢀ2014ꢀ
Publishedꢀ20ꢀJanuaryꢀ2015ꢀ
Keywords:ꢀ
Rhodium(III)ꢀ
C–Hꢀactivationꢀ
Benzamidesꢀ
Arylquinonesꢀ
1.ꢀ ꢀ Introductionꢀ
Onꢀtheꢀotherꢀhand,ꢀquinonesꢀrepresentꢀanꢀimportantꢀclassꢀofꢀ
biologicallyꢀactiveꢀmoleculesꢀthatꢀareꢀwidelyꢀdistributedꢀinꢀnat‐
Transition‐metal‐catalyzedꢀ directꢀ functionalizationꢀ ofꢀ C–Hꢀ
uralꢀ productsꢀ [64–67].ꢀ Bothꢀ naturalꢀ andꢀ syntheticꢀ medicinalꢀ
agentsꢀ haveꢀ beenꢀ developedꢀ thatꢀ areꢀ basedꢀ onꢀ theꢀ quinoneꢀ
structureꢀ dueꢀ toꢀ theirꢀ chemotherapeuticꢀ valueꢀ suchꢀ asꢀ anti‐
tumor,ꢀantifungal,ꢀandꢀantibacterialꢀ[68–72].ꢀTheꢀquinoneꢀmoi‐
etyꢀisꢀalsoꢀinvolvedꢀinꢀmanyꢀbioenergeticꢀprocessesꢀandꢀplaysꢀaꢀ
vitalꢀroleꢀinꢀelectron‐transportꢀprocessesꢀ[73].ꢀAryl‐substitutedꢀ
quinonesꢀareꢀveryꢀusefulꢀinꢀphotosynthesisꢀandꢀtheꢀdyeꢀindus‐
tryꢀ owingꢀ toꢀ theirꢀ uniqueꢀ visualꢀ andꢀ electronicꢀ propertiesꢀ
[74,75].ꢀ Thus,ꢀ developingꢀ powerfulꢀ syntheticꢀ methodsꢀ ofꢀ ar‐
ylquinonesꢀ isꢀ veryꢀ necessaryꢀ toꢀ fulfillꢀ theꢀ practicalꢀ require‐
ments.ꢀ Arylationꢀ ofꢀ quinonesꢀ hasꢀ beenꢀ reportedꢀ byꢀ someꢀ
groupsꢀ[76–90].ꢀHowever,ꢀtheseꢀapproachesꢀoftenꢀsufferꢀfromꢀ
poorꢀ atom‐economy,ꢀ substrateꢀ limitations,ꢀ stoichiometricꢀ
amountsꢀ ofꢀ metalsꢀ orꢀ highꢀ temperature.ꢀ Althoughꢀ muchꢀ pro‐
gressꢀhasꢀbeenꢀmade,ꢀtheꢀdevelopmentꢀofꢀnewꢀsyntheticꢀmeth‐
odsꢀisꢀstillꢀnecessary,ꢀespeciallyꢀviaꢀaꢀC–Hꢀactivationꢀpathway.ꢀ
Hereinꢀ weꢀ reportꢀ Rh(III)‐catalyzedꢀ C–Hꢀ activationꢀ ofꢀ
bondsꢀ hasꢀ becomeꢀ anꢀ increasinglyꢀ importantꢀ strategyꢀ forꢀ theꢀ
constructionꢀ ofꢀ complexꢀ organicꢀ moleculesꢀ [1–3].ꢀ Palladium,ꢀ
ruthenium,ꢀiridium,ꢀandꢀcopperꢀcatalystsꢀareꢀparticularlyꢀwellꢀ
ꢀ
knownꢀtoꢀserveꢀthisꢀpurposeꢀ[4–19]. Althoughꢀmuchꢀprogressꢀ
hasꢀbeenꢀmade,ꢀtheꢀdevelopmentꢀofꢀnewꢀsyntheticꢀmethodsꢀisꢀ
III
stillꢀnecessary,ꢀespeciallyꢀviaꢀaꢀC–Hꢀactivationꢀpathway.ꢀRh Cp*ꢀ
representꢀoneꢀofꢀtheꢀmostꢀfrequentlyꢀusedꢀcatalystsꢀthatꢀena‐
bledꢀaꢀvastꢀnumberꢀofꢀtransformationsꢀthroughꢀcouplingꢀofꢀC–Hꢀ
bondsꢀwithꢀalkenesꢀalongꢀwithꢀotherꢀmoleculesꢀ[20–57].ꢀHow‐
ever,ꢀtheꢀolefinsꢀ areꢀmostlyꢀlimitedꢀtoꢀ acrylatesꢀandꢀ styrenes.ꢀ
Thereꢀareꢀonlyꢀaꢀfewꢀreportsꢀonꢀtheꢀapplicationsꢀofꢀquinonesꢀasꢀ
anꢀolefinꢀpartnerꢀunderꢀoxidativeꢀconditionsꢀ[58].ꢀTheꢀrarityꢀisꢀ
probablyꢀdueꢀtoꢀtheꢀdifficultyꢀofꢀβ‐hydrideꢀeliminationꢀfollow‐
ingꢀsynꢀmigratoryꢀinsertionꢀofꢀaꢀRh–CꢀbondꢀintoꢀtheꢀC=Cꢀbondꢀ
ofꢀaꢀquinone.ꢀInꢀaddition,ꢀtheꢀstericꢀeffectꢀofꢀthisꢀspecialꢀdisub‐
stitutedꢀolefinꢀmayꢀalsoꢀbeꢀaccountableꢀ[59–63].ꢀ ꢀ
*ꢀCorrespondingꢀauthor.ꢀTel:ꢀ+86‐411‐84379089;ꢀE‐mail:ꢀxwli@dicp.ac.cnꢀ ꢀ ꢀ
ThisꢀworkꢀwasꢀsupportedꢀbyꢀtheꢀDalianꢀInstituteꢀofꢀChemicalꢀPhysics,ꢀChineseꢀAcademyꢀofꢀSciencesꢀandꢀtheꢀNationalꢀNaturalꢀScienceꢀFoundationꢀofꢀ
Chinaꢀ(21272231).ꢀ ꢀ
DOI:ꢀ10.1016/S1872‐2067(14)60245‐Xꢀ|ꢀhttp://www.sciencedirect.com/science/journal/18722067ꢀ|ꢀChin.ꢀJ.ꢀCatal.,ꢀVol.ꢀ36,ꢀNo.ꢀ1,ꢀJanuaryꢀ2015ꢀ ꢀ ꢀ

ꢀ
ZisongꢀQiꢀetꢀal.ꢀ/ꢀChineseꢀJournalꢀofꢀCatalysisꢀ36ꢀ(2015)ꢀ48–56ꢀ
49ꢀ
N‐(alkyl)benzamidesꢀinꢀtheꢀcouplingꢀwithꢀquinones,ꢀleadingꢀtoꢀ
synthesisꢀofꢀarylatedꢀquinones.ꢀ
N‐(tert‐butyl)‐5‐methoxy‐2',5'‐dioxo‐2',5'‐dihydro‐[1,1'‐
1
biphenyl]‐2‐carboxamideꢀ (3c).ꢀ Hꢀ NMRꢀ (400ꢀ MHz,ꢀ CDCl
.46ꢀ(d,ꢀJꢀ=ꢀ8.5ꢀHz,ꢀ1H),ꢀ6.92ꢀ(dd,ꢀJꢀ=ꢀ8.5,ꢀ2.6ꢀHz,ꢀ1H),ꢀ6.80ꢀ(dd,ꢀJꢀ=ꢀ
4.1,ꢀ2.2ꢀHz,ꢀ3H),ꢀ6.72ꢀ(d,ꢀJꢀ=ꢀ1.5ꢀHz,ꢀ1H),ꢀ5.93ꢀ(s,ꢀ1H),ꢀ3.84ꢀ(s,ꢀ
H),ꢀ 1.37ꢀ (s,ꢀ 9H).ꢀ 13Cꢀ NMRꢀ (100ꢀ MHz,ꢀ CDCl
)ꢀ δꢀ 187.6,ꢀ 185.7,ꢀ
3
)ꢀ δꢀ
7
2.ꢀ ꢀ Experimentalꢀ
3
3
2.1.ꢀ ꢀ Generalꢀ ꢀ
168.1,ꢀ 161.4,ꢀ 149.8,ꢀ 137.2,ꢀ 136.9,ꢀ 135.2,ꢀ 131.0,ꢀ 130.0,ꢀ 128.1,ꢀ
+
116.3,ꢀ 114.4,ꢀ 55.7,ꢀ 51.9,ꢀ 28.8.ꢀ HRMS:ꢀ [Mꢀ +ꢀ H] ꢀ calculatedꢀ forꢀ
AllꢀreactionsꢀwereꢀcarriedꢀoutꢀusingꢀSchlenkꢀtechniquesꢀorꢀ
C
18
H
20NO :ꢀ314.1392,ꢀfoundꢀ314.1391.ꢀ ꢀ
4
inꢀaꢀnitrogen‐filledꢀglovebox.ꢀNMRꢀspectraꢀwereꢀrecordedꢀonꢀaꢀ
Brukerꢀ400ꢀMHzꢀNMRꢀspectrometerꢀinꢀtheꢀsolventsꢀindicated.ꢀ
Theꢀ chemicalꢀ shiftꢀ isꢀ givenꢀ inꢀ dimensionlessꢀ δꢀ valuesꢀ andꢀ isꢀ
frequencyꢀreferencedꢀrelativeꢀtoꢀTMSꢀinꢀ Hꢀandꢀ CꢀNMRꢀspec‐
troscopy.ꢀHRMSꢀdataꢀwereꢀobtainedꢀonꢀanꢀAgilentꢀ6540ꢀQ‐Tof.ꢀ
Columnꢀchromatographyꢀwasꢀperformedꢀonꢀsilicaꢀgelꢀ(300–400ꢀ
mesh)ꢀ usingꢀ ethylꢀ acetateꢀ (EA)/petroleumꢀ etherꢀ (PE).ꢀ Allꢀ
chemicalsꢀ wereꢀ obtainedꢀ fromꢀ commercialꢀ sourcesꢀ andꢀ wereꢀ
usedꢀasꢀreceivedꢀunlessꢀotherwiseꢀnoted.ꢀ
N‐(tert‐butyl)‐5‐fluoro‐2',5'‐dioxo‐2',5'‐dihydro‐[1,1'‐
1
biphenyl]‐2‐carboxamideꢀ (3d).ꢀ Hꢀ NMRꢀ (400ꢀ MHz,ꢀ CDCl
3
)ꢀ δꢀ
7.53ꢀ(dd,ꢀJꢀ=ꢀ8.5,ꢀ5.4ꢀHz,ꢀ1H),ꢀ7.13ꢀ(td,ꢀJꢀ=ꢀ8.3,ꢀ2.6ꢀHz,ꢀ1H),ꢀ7.01ꢀ
(dd,ꢀJꢀ=ꢀ8.8,ꢀ2.6ꢀHz,ꢀ1H),ꢀ6.82ꢀ(d,ꢀJꢀ=ꢀ1.0ꢀHz,ꢀ2H),ꢀ6.73ꢀ(s,ꢀ1H),ꢀ5.94ꢀ
1
13
13
(s,ꢀ1H),ꢀ1.37ꢀ(s,ꢀ9H).ꢀ CꢀNMRꢀ(100ꢀMHz,ꢀCDCl )ꢀδꢀ187.3,ꢀ185.4,ꢀ
3
167.5,ꢀ163.7ꢀ(d,ꢀJꢀ=ꢀ250.9ꢀHz),ꢀ148.3ꢀ(d,ꢀJꢀ=ꢀ1.5ꢀHz),ꢀ137.1,ꢀ137.0,ꢀ
135.7ꢀ(d,ꢀJꢀ=ꢀ8.2ꢀHz),ꢀ134.0ꢀ(d,ꢀJꢀ=ꢀ3.4ꢀHz),ꢀ131.7,ꢀ128.6ꢀ(d,ꢀJꢀ=ꢀ8.7ꢀ
Hz),ꢀ 117.7ꢀ (d,ꢀ Jꢀ=ꢀ22.9ꢀHz),ꢀ116.3ꢀ(d,ꢀJꢀ =ꢀ 21.1ꢀ Hz),ꢀ 52.2,ꢀ 28.7.ꢀ
+
HRMS:ꢀ [Mꢀ +ꢀ H] ꢀ calculatedꢀ forꢀ C17
H
17FNO :ꢀ 302.1192,ꢀ foundꢀ
3
302.1181.ꢀ
2.2.ꢀ ꢀ Preparationꢀofꢀcompoundsꢀ
N‐(tert‐butyl)‐5‐chloro‐2',5'‐dioxo‐2',5'‐dihydro‐[1,1'‐
1
biphenyl]‐2‐carboxamideꢀ (3e).ꢀ Hꢀ NMRꢀ (400ꢀ MHz,ꢀ CDCl
3
)ꢀ δꢀ
2.2.1.ꢀ ꢀ Generalꢀprocedureꢀforꢀtheꢀsynthesisꢀofꢀcompoundsꢀ3ꢀ
N‐(alkyl)benzamidesꢀ (0.2ꢀ mmol),ꢀ quinonesꢀ (0.3ꢀ mmol),ꢀ
7.47ꢀ(d,ꢀJꢀ=ꢀ8.2ꢀHz,ꢀ1H),ꢀ7.41ꢀ(dd,ꢀJꢀ=ꢀ8.2,ꢀ2.0ꢀHz,ꢀ1H),ꢀ7.28ꢀ(d,ꢀJꢀ=ꢀ
2.1ꢀHz,ꢀ1H),ꢀ6.81ꢀ(s,ꢀ2H),ꢀ6.74ꢀ(s,ꢀ1H),ꢀ5.97ꢀ(s,ꢀ1H),ꢀ1.37ꢀ(s,ꢀ9H).ꢀ
13CꢀNMRꢀ(100ꢀMHz,ꢀCDCl
)ꢀδꢀ187.2,ꢀ185.4,ꢀ167.5,ꢀ148.1,ꢀ137.1,ꢀ
2 2 6 2 3
[RhCp*Cl ] ꢀ(4ꢀmol%),ꢀAgSbF ꢀ(16ꢀmol%),ꢀAg CO ꢀ(2.0ꢀequiv)ꢀ
3
andꢀ dioxaneꢀ (3ꢀ mL)ꢀ wereꢀ chargedꢀ intoꢀ theꢀ sealedꢀ tube.ꢀ Theꢀ
reactionꢀmixtureꢀwasꢀstirredꢀatꢀ100ꢀ°Cꢀforꢀ12ꢀh.ꢀAfterꢀcooledꢀtoꢀ
roomꢀ temperature,ꢀ theꢀ solventꢀ wasꢀ removedꢀ underꢀ reducedꢀ
pressureꢀandꢀtheꢀresidueꢀwasꢀpurifiedꢀbyꢀsilicaꢀgelꢀchromatog‐
raphyꢀusingꢀPE/EAꢀtoꢀaffordꢀcompoundsꢀ3.ꢀ
137.0,ꢀ136.8,ꢀ136.1,ꢀ134.9,ꢀ131.7,ꢀ130.4,ꢀ129.7,ꢀ127.9,ꢀ52.2,ꢀ28.7.ꢀ
+
HRMS:ꢀ [Mꢀ +ꢀ H] ꢀ calculatedꢀ forꢀ C17
H
17ClNO :ꢀ 318.0897,ꢀ foundꢀ
3
318.0898.ꢀ
5‐Bromo‐N‐(tert‐butyl)‐2',5'‐dioxo‐2',5'‐dihydro‐[1,1'‐
1
biphenyl]‐2‐carboxamideꢀ (3f).ꢀ Hꢀ NMRꢀ (400ꢀ MHz,ꢀ CDCl
3
)ꢀ δꢀ
7
.58ꢀ(dd,ꢀJꢀ=ꢀ8.2,ꢀ2.0ꢀHz,ꢀ1H),ꢀ7.44ꢀ(d,ꢀJꢀ=ꢀ1.9ꢀHz,ꢀ1H),ꢀ7.39ꢀ(d,ꢀJꢀ=ꢀ
8.2ꢀHz,ꢀ1H),ꢀ6.81ꢀ(s,ꢀ2H),ꢀ6.74ꢀ(s,ꢀ1H),ꢀ5.95ꢀ(s,ꢀ1H),ꢀ1.37ꢀ(s,ꢀ9H).ꢀ
13CꢀNMRꢀ(100ꢀMHz,ꢀCDCl
)ꢀδꢀ187.2,ꢀ185.4,ꢀ167.6,ꢀ148.0,ꢀ137.1,ꢀ
2
.2.2.ꢀ ꢀ Generalꢀprocedureꢀforꢀtheꢀsynthesisꢀofꢀcompoundsꢀ4ꢀ
N‐(tert‐butyl)benzamidesꢀ(0.2ꢀmmol),ꢀquinonesꢀ(0.3ꢀmmol),ꢀ
3
[
RhCp*Cl
2
]
2
ꢀ (4ꢀ mol%),ꢀ AgSbF
6
ꢀ (30ꢀ mol%),ꢀ AgOAcꢀ (0.2ꢀ equiv)ꢀ
137.0,ꢀ136.5,ꢀ135.0,ꢀ133.3,ꢀ132.7,ꢀ131.8,ꢀ128.0,ꢀ124.9,ꢀ52.3,ꢀ28.7.ꢀ
+
andꢀ acetoneꢀ (4ꢀ mL)ꢀ wereꢀ chargedꢀ intoꢀ theꢀ sealedꢀ tube.ꢀ Theꢀ
reactionꢀmixtureꢀwasꢀstirredꢀatꢀ100ꢀ°Cꢀforꢀ12ꢀh.ꢀAfterꢀcooledꢀtoꢀ
roomꢀ temperature,ꢀ theꢀ solventꢀ wasꢀ removedꢀ underꢀ reducedꢀ
pressureꢀandꢀtheꢀresidueꢀwasꢀpurifiedꢀbyꢀsilicaꢀgelꢀchromatog‐
raphyꢀusingꢀetroleumꢀether/ethylꢀacetateꢀtoꢀaffordꢀcompoundsꢀ
HRMS:ꢀ [Mꢀ +ꢀ H] ꢀcalculatedꢀforꢀC17
H
17BrNO :ꢀ 362.0392,ꢀ foundꢀ
3
362.0391.ꢀ
N‐(tert‐butyl)‐2'',5''‐dioxo‐2'',5''‐dihydro‐[1,1':3',1''‐
1
terphenyl]‐4'‐carboxamideꢀ(3g).ꢀ HꢀNMRꢀ(400ꢀMHz,ꢀCDCl
3
)ꢀδꢀ
7.65ꢀ(dd,ꢀJꢀ=ꢀ7.9,ꢀ1.6ꢀHz,ꢀ1H),ꢀ7.61–7.54ꢀ(m,ꢀ3H),ꢀ7.49–7.43ꢀ(m,ꢀ
3H),ꢀ7.39ꢀ(t,ꢀJꢀ=ꢀ7.2ꢀHz,ꢀ1H),ꢀ6.82ꢀ(s,ꢀ2H),ꢀ6.80ꢀ(d,ꢀJꢀ=ꢀ1.3ꢀHz,ꢀ1H),ꢀ
4
.ꢀ
13
6
.04ꢀ(s,ꢀ1H),ꢀ1.40ꢀ(s,ꢀ9H).ꢀ CꢀNMRꢀ(100ꢀMHz,ꢀCDCl
3
)ꢀδꢀ187.6,ꢀ
2.3.ꢀ ꢀ Spectralꢀdataꢀforꢀproductsꢀ
185.9,ꢀ 168.2,ꢀ 149.6,ꢀ 144.0,ꢀ 139.5,ꢀ 137.1,ꢀ 137.1,ꢀ 136.3,ꢀ 133.8,ꢀ
1
31.4,ꢀ 129.3,ꢀ 129.2,ꢀ 128.4,ꢀ 128.3,ꢀ 127.3,ꢀ 127.1,ꢀ 52.1,ꢀ 28.8.ꢀ
+
N‐(tert‐butyl)‐2',5'‐dioxo‐2',5'‐dihydro‐[1,1'‐biphenyl]‐2‐
HRMS:ꢀ [Mꢀ +ꢀ H] ꢀ calculatedꢀ forꢀ C23
H
22NO :ꢀ 360.1600,ꢀ foundꢀ
3
1
carboxamideꢀ(3a).ꢀ HꢀNMRꢀ(400ꢀMHz,ꢀCDCl
3
)ꢀδꢀ7.53ꢀ(dd,ꢀJꢀ=ꢀ7.4,ꢀ
360.1600.ꢀ
1
1
6
.5ꢀHz,ꢀ1H),ꢀ7.48ꢀ(dd,ꢀJꢀ=ꢀ7.4,ꢀ1.6ꢀHz,ꢀ1H),ꢀ7.44ꢀ(td,ꢀJꢀ=ꢀ7.5,ꢀ1.5ꢀHz,ꢀ
H),ꢀ7.29ꢀ(dd,ꢀJꢀ=ꢀ7.4,ꢀ1.2ꢀHz,ꢀ1H),ꢀ6.80ꢀ(d,ꢀJꢀ=ꢀ1.1ꢀHz,ꢀ2H),ꢀ6.75ꢀ–ꢀ
.72ꢀ (m,ꢀ 1H),ꢀ 6.01ꢀ (s,ꢀ 1H),ꢀ 1.38ꢀ (s,ꢀ 9H).ꢀ 13Cꢀ NMRꢀ (100ꢀ MHz,ꢀ
N‐(tert‐butyl)‐2',5'‐dioxo‐5‐(trifluoromethyl)‐2',5'‐dihydro‐
1
[1,1'‐biphenyl]‐2‐carboxamideꢀ(3h).ꢀ HꢀNMRꢀ(400ꢀMHz,ꢀCDCl
3
)ꢀ
δꢀ7.72ꢀ(dd,ꢀJꢀ=ꢀ8.0,ꢀ1.0ꢀHz,ꢀ1H),ꢀ7.64ꢀ(d,ꢀJꢀ=ꢀ8.0ꢀHz,ꢀ1H),ꢀ7.55ꢀ(s,ꢀ
CDCl )ꢀ δꢀ 187.6,ꢀ 185.8,ꢀ 168.4,ꢀ 149.5,ꢀ 137.6,ꢀ 137.03,ꢀ 136.97,ꢀ
3
1H),ꢀ6.84ꢀ(d,ꢀJꢀ=ꢀ2.2ꢀHz,ꢀ2H),ꢀ6.80ꢀ(d,ꢀJꢀ=ꢀ2.1ꢀHz,ꢀ1H),ꢀ5.97ꢀ(s,ꢀ1H),ꢀ
13
1
33.2,ꢀ131.3,ꢀ130.9,ꢀ130.4,ꢀ129.8,ꢀ126.5,ꢀ52.0,ꢀ28.7.ꢀHRMS:ꢀ[Mꢀ+ꢀ
1.39ꢀ(s,ꢀ9H).ꢀ CꢀNMRꢀ(100ꢀMHz,ꢀCDCl )ꢀδꢀ187.1,ꢀ185.4,ꢀ167.3,ꢀ
3
+
H] ꢀcalculatedꢀforꢀC
7 3
H18NO :ꢀ284.1287,ꢀfoundꢀ284.1290.ꢀ
147.9,ꢀ140.9,ꢀ137.3,ꢀ136.9,ꢀ134.0,ꢀ132.9ꢀ(q,ꢀJꢀ=ꢀ33.2ꢀHz),ꢀ132.2,ꢀ
127.4ꢀ(q,ꢀJꢀ=ꢀ3.6ꢀHz),ꢀ127.1,ꢀ126.7ꢀ(q,ꢀJꢀ=ꢀ3.7ꢀHz),ꢀ123.4ꢀ(q,ꢀJꢀ=ꢀ
N‐(tert‐butyl)‐5‐methyl‐2',5'‐dioxo‐2',5'‐dihydro‐[1,1'‐
1
+
biphenyl]‐2‐carboxamideꢀ (3b).ꢀ Hꢀ NMRꢀ (400ꢀ MHz,ꢀ CDCl
3
)ꢀ δꢀ
267.7ꢀ Hz),ꢀ 52.5,ꢀ 28.7.ꢀ HRMS:ꢀ [Mꢀ +ꢀ H] ꢀ calculatedꢀ forꢀ
7
.42ꢀ(d,ꢀJꢀ=ꢀ7.8ꢀHz,ꢀ1H),ꢀ7.24ꢀ(d,ꢀJꢀ=ꢀ7.8ꢀHz,ꢀ1H),ꢀ7.09ꢀ(s,ꢀ1H),ꢀ6.80ꢀ
C
18
H
17
F
3
NO
3
:ꢀ352.1161,ꢀfoundꢀ352.1157.ꢀ
13
ꢀ
(s,ꢀ2H),ꢀ6.72ꢀ(s,ꢀ1H),ꢀ5.96ꢀ(s,ꢀ1H),ꢀ2.39ꢀ(s,ꢀ3H),ꢀ1.37ꢀ(s,ꢀ9H).ꢀ Cꢀ
Methyl 6‐(tert‐butylcarbamoyl)‐2',5'‐dioxo‐2',5'‐dihydro‐[1,1'‐ꢀ
1
NMRꢀ (100ꢀ MHz,ꢀ CDCl )ꢀ δꢀ 187.6,ꢀ 185.9,ꢀ 168.4,ꢀ 149.8,ꢀ 141.3,ꢀ
3
biphenyl]‐3‐carboxylateꢀ(3i).ꢀ HꢀNMRꢀ(400ꢀMHz,ꢀCDCl
3
)ꢀδꢀ8.10ꢀ
1
2
2
37.1,ꢀ137.0,ꢀ134.9,ꢀ133.3,ꢀ131.2,ꢀ131.0,ꢀ130.3,ꢀ126.5,ꢀ51.9,ꢀ28.8,ꢀ
(dd,ꢀJꢀ=ꢀ8.0,ꢀ1.4ꢀHz,ꢀ1H),ꢀ7.96ꢀ(d,ꢀJꢀ=ꢀ1.2ꢀHz,ꢀ1H),ꢀ7.59ꢀ(d,ꢀJꢀ=ꢀ8.0ꢀ
Hz,ꢀ1H),ꢀ6.81ꢀ(d,ꢀJꢀ=ꢀ6.4ꢀHz,ꢀ3H),ꢀ6.04ꢀ(s,ꢀ1H),ꢀ3.94ꢀ(s,ꢀ3H),ꢀ1.39ꢀ
+
1.4.ꢀHRMS:ꢀ[Mꢀ+ꢀH] ꢀcalculatedꢀforꢀC18
H
20NO :ꢀ298.1443,ꢀfoundꢀ
3
13
98.1440.ꢀ ꢀ
(s,ꢀ9H).ꢀ CꢀNMRꢀ(100ꢀMHz,ꢀCDCl )ꢀδꢀ187.3,ꢀ185.6,ꢀ167.7,ꢀ165.8,ꢀ
3

50ꢀ
ZisongꢀQiꢀetꢀal.ꢀ/ꢀChineseꢀJournalꢀofꢀCatalysisꢀ36ꢀ(2015)ꢀ48–56ꢀ
1
1
C
48.4,ꢀ 141.5,ꢀ 137.2,ꢀ 136.9,ꢀ 133.4,ꢀ 132.3,ꢀ 132.0,ꢀ 131.5,ꢀ 131.0,ꢀ
165.0,ꢀ 156.5,ꢀ 150.9,ꢀ 137.2,ꢀ 136.9,ꢀ 136.1,ꢀ 131.4,ꢀ 129.8,ꢀ 125.2,ꢀ
+
+
26.7,ꢀ 52.7,ꢀ 52.4,ꢀ 28.7.ꢀ HRMS:ꢀ [Mꢀ +ꢀ H] ꢀ calculatedꢀ forꢀ
:ꢀ342.1341,ꢀfoundꢀ342.1340.ꢀ
123.3,ꢀ 113.4,ꢀ 56.5,ꢀ 51.7,ꢀ 28.9.ꢀ HRMS:ꢀ [Mꢀ +ꢀ H] ꢀ calculatedꢀ forꢀ
:ꢀ314.1392,ꢀfoundꢀ314.1398.ꢀ
19
H
20NO
5
C
18
H
20NO
4
N‐(tert‐butyl)‐4‐methyl‐2',5'‐dioxo‐2',5'‐dihydro‐[1,1'‐
N‐(tert‐butyl)‐3‐fluoro‐2',5'‐dioxo‐2',5'‐dihydro‐[1,1'‐
1
1
biphenyl]‐2‐carboxamideꢀ (3j).ꢀ Hꢀ NMRꢀ (400ꢀ MHz,ꢀ CDCl
3
)ꢀ δꢀ
biphenyl]‐2‐carboxamideꢀ (3o).ꢀ Hꢀ NMRꢀ (400ꢀ MHz,ꢀ CDCl
3
)ꢀ δꢀ
7
.33ꢀ(s,ꢀ1H),ꢀ7.29ꢀ(d,ꢀJꢀ=ꢀ8.6ꢀHz,ꢀ1H),ꢀ7.17ꢀ(d,ꢀJꢀ=ꢀ7.7ꢀHz,ꢀ1H),ꢀ6.78ꢀ
7.48–7.41ꢀ(m,ꢀ1H),ꢀ7.20ꢀ(ddd,ꢀJꢀ=ꢀ10.2,ꢀ8.4,ꢀ0.9ꢀHz,ꢀ1H),ꢀ7.09ꢀ(dd,ꢀ
Jꢀ=ꢀ7.6,ꢀ0.7ꢀHz,ꢀ1H),ꢀ6.81ꢀ(d,ꢀJꢀ=ꢀ1.2ꢀHz,ꢀ2H),ꢀ6.73ꢀ(t,ꢀJꢀ=ꢀ1.1ꢀHz,ꢀ
13
(s,ꢀ2H),ꢀ6.71ꢀ(s,ꢀ1H),ꢀ6.00ꢀ(s,ꢀ1H),ꢀ2.41ꢀ(s,ꢀ3H),ꢀ1.38ꢀ(s,ꢀ9H).ꢀ Cꢀ
NMRꢀ (100ꢀ MHz,ꢀ CDCl )ꢀ δꢀ 187.6,ꢀ 186.0,ꢀ 168.5,ꢀ 149.4,ꢀ 140.2,ꢀ
1H),ꢀ 6.23ꢀ (s,ꢀ 1H),ꢀ 1.38ꢀ (s,ꢀ 9H).ꢀ 13Cꢀ NMRꢀ (100ꢀ MHz,ꢀ CDCl
)ꢀ δꢀ
3
3
1
2
2
37.6,ꢀ137.0,ꢀ136.9,ꢀ131.4,ꢀ131.0,ꢀ130.4,ꢀ130.2,ꢀ127.3,ꢀ51.9,ꢀ28.7,ꢀ
187.5,ꢀ185.4,ꢀ163.0ꢀ(d,ꢀJꢀ=ꢀ1.8ꢀHz),ꢀ159.3ꢀ(d,ꢀJꢀ=ꢀ245.7ꢀHz),ꢀ148.8ꢀ
(d,ꢀJꢀ=ꢀ2.4ꢀHz),ꢀ137.1,ꢀ137.0,ꢀ136.2ꢀ(d,ꢀJꢀ=ꢀ3.5ꢀHz),ꢀ131.9ꢀ(d,ꢀJꢀ=ꢀ9.7ꢀ
Hz),ꢀ131.4,ꢀ126.4ꢀ(d,ꢀJꢀ=ꢀ2.9ꢀHz),ꢀ124.7ꢀ(d,ꢀJꢀ=ꢀ15.8ꢀHz),ꢀ117.7ꢀ(d,ꢀJꢀ
+
1.3.ꢀHRMS:ꢀ[Mꢀ+ꢀH] ꢀcalculatedꢀforꢀC18
H
20NO :ꢀ298.1443,ꢀfoundꢀ
3
98.1446.ꢀ
+
N‐(tert‐butyl)‐4‐methoxy‐2',5'‐dioxo‐2',5'‐dihydro‐[1,1'‐
=ꢀ 24.5ꢀ Hz),ꢀ 52.4,ꢀ 28.8.ꢀ HRMS:ꢀ [Mꢀ +ꢀ H] ꢀ calculatedꢀ forꢀ
1
biphenyl]‐2‐carboxamideꢀ (3k).ꢀ Hꢀ NMRꢀ (400ꢀ MHz,ꢀ CDCl
3
)ꢀ δꢀ
C
17
H
17FNO :ꢀ302.1192,ꢀfoundꢀ302.1194.ꢀ
3
7
2
.23ꢀ(d,ꢀJꢀ=ꢀ8.4ꢀHz,ꢀ1H),ꢀ7.05ꢀ(d,ꢀJꢀ=ꢀ2.5ꢀHz,ꢀ1H),ꢀ7.00ꢀ(dd,ꢀJꢀ=ꢀ8.4,ꢀ
.6ꢀHz,ꢀ1H),ꢀ6.79ꢀ(d,ꢀJꢀ=ꢀ1.1ꢀHz,ꢀ2H),ꢀ6.72ꢀ(d,ꢀJꢀ=ꢀ1.1ꢀHz,ꢀ1H),ꢀ5.91ꢀ
N‐(tert‐butyl)‐3‐(3,6‐dioxocyclohexa‐1,4‐dien‐1‐yl)‐2‐
1
3
naphthamideꢀ(3p).ꢀ HꢀNMRꢀ(400ꢀMHz,ꢀCDCl )ꢀδꢀ7.97ꢀ(s,ꢀ1H),ꢀ
13
(s,ꢀ1H),ꢀ3.87ꢀ(s,ꢀ3H),ꢀ1.37ꢀ(s,ꢀ9H).ꢀ CꢀNMRꢀ(100ꢀMHz,ꢀCDCl
3
)ꢀδꢀ
7.87ꢀ(dd,ꢀJꢀ=ꢀ11.5,ꢀ4.7ꢀHz,ꢀ2H),ꢀ7.78ꢀ(s,ꢀ1H),ꢀ7.62–7.55ꢀ(m,ꢀ2H),ꢀ
13
1
1
87.7,ꢀ 186.2,ꢀ 168.2,ꢀ 160.9,ꢀ 149.0,ꢀ 139.2,ꢀ 137.1,ꢀ 137.0,ꢀ 131.9,ꢀ
30.9,ꢀ125.3,ꢀ115.1,ꢀ113.6,ꢀ55.9,ꢀ52.1,ꢀ28.8.ꢀHRMS:ꢀ[Mꢀ+ꢀH] ꢀcal‐
:ꢀ314.1392,ꢀfoundꢀ314.1394.ꢀ
6.86ꢀ (s,ꢀ 1H),ꢀ 6.81ꢀ (s,ꢀ 2H),ꢀ 6.18ꢀ (s,ꢀ 1H),ꢀ 1.43ꢀ (s,ꢀ 9H).ꢀ Cꢀ NMRꢀ
(100ꢀ MHz,ꢀ CDCl )ꢀ δꢀ 187.8,ꢀ 186.4,ꢀ 168.7,ꢀ 149.7,ꢀ 137.1,ꢀ 137.0,ꢀ
+
3
culatedꢀforꢀC18
H20NO
4
135.1,ꢀ 133.9,ꢀ 133.1,ꢀ 131.2,ꢀ 130.8,ꢀ 130.4,ꢀ 128.4,ꢀ 128.3,ꢀ 128.2,ꢀ
+
N‐(tert‐butyl)‐6‐methoxy‐2',5'‐dioxo‐2',5'‐dihydro‐[1,1'‐
128.1,ꢀ 126.5,ꢀ 52.1,ꢀ 28.8.ꢀ HRMS:ꢀ [Mꢀ +ꢀ H] ꢀ calculatedꢀ forꢀ
1
biphenyl]‐2‐carboxamideꢀ (3k’).ꢀ Hꢀ NMRꢀ (400ꢀ MHz,ꢀ CDCl
3
)ꢀ δꢀ
C
21
H
20NO :ꢀ334.1443,ꢀfoundꢀ334.1442.ꢀ
3
7
1
.38ꢀ(t,ꢀJꢀ=ꢀ8.0ꢀHz,ꢀ1H),ꢀ7.11ꢀ(d,ꢀJꢀ=ꢀ7.7ꢀHz,ꢀ1H),ꢀ7.02ꢀ(d,ꢀJꢀ=ꢀ8.4ꢀHz,ꢀ
H),ꢀ6.84ꢀ(d,ꢀJꢀ=ꢀ10.1ꢀHz,ꢀ1H),ꢀ6.80ꢀ(dd,ꢀJꢀ=ꢀ10.1,ꢀ2.4ꢀHz,ꢀ1H),ꢀ6.74ꢀ
N‐(tert‐butyl)‐3‐(3,6‐dioxocyclohexa‐1,4‐dien‐1‐yl)thiophene‐
1
3
2‐carboxamideꢀ(3q).ꢀ HꢀNMRꢀ(400ꢀMHz,ꢀCDCl )ꢀδꢀ7.35ꢀ(d,ꢀJꢀ=ꢀ5.0ꢀ
13
(d,ꢀJꢀ=ꢀ2.4ꢀHz,ꢀ1H),ꢀ5.70ꢀ(s,ꢀ1H),ꢀ3.77ꢀ(s,ꢀ3H),ꢀ1.32ꢀ(s,ꢀ9H).ꢀ Cꢀ
Hz,ꢀ1H),ꢀ6.99ꢀ(d,ꢀJꢀ=ꢀ5.0ꢀHz,ꢀ1H),ꢀ6.86ꢀ(d,ꢀJꢀ=ꢀ10.1ꢀHz,ꢀ1H),ꢀ6.80ꢀ
(dd,ꢀJꢀ=ꢀ10.1,ꢀ2.3ꢀHz,ꢀ1H),ꢀ6.75ꢀ(d,ꢀJꢀ=ꢀ2.3ꢀHz,ꢀ1H),ꢀ5.79ꢀ(s,ꢀ1H),ꢀ
NMRꢀ (100ꢀ MHz,ꢀ CDCl )ꢀ δꢀ 187.5,ꢀ 186.3,ꢀ 168.1,ꢀ 157.4,ꢀ 144.8,ꢀ
3
13
1
2
3
39.2,ꢀ137.1,ꢀ136.8,ꢀ134.4,ꢀ130.6,ꢀ121.0,ꢀ118.9,ꢀ113.0,ꢀ56.2,ꢀ52.0,ꢀ
8.7.ꢀHRMS:ꢀ[Mꢀ+ꢀH] ꢀcalculatedꢀforꢀC18
14.1395.ꢀ
1.39ꢀ(s,ꢀ9H).ꢀ CꢀNMRꢀ(100ꢀMHz,ꢀCDCl )ꢀδꢀ187.4,ꢀ185.0,ꢀ161.4,ꢀ
3
+
4
H20NO :ꢀ314.1392,ꢀfoundꢀ
143.6,ꢀ137.6,ꢀ137.2,ꢀ136.6,ꢀ134.9,ꢀ132.1,ꢀ129.7,ꢀ126.5,ꢀ52.4,ꢀ28.8.ꢀ
+
HRMS:ꢀ [Mꢀ +ꢀ H] ꢀ calculatedꢀ forꢀ C15
H
16NO S:ꢀ 290.0851,ꢀ foundꢀ
3
N‐(tert‐butyl)‐4‐chloro‐2',5'‐dioxo‐2',5'‐dihydro‐[1,1'‐
290.0849.ꢀ
1
biphenyl]‐2‐carboxamideꢀ (3l).ꢀ Hꢀ NMRꢀ (400ꢀ MHz,ꢀ CDCl
3
)ꢀ δꢀ
N‐(tert‐butyl)‐2‐(1,4‐dioxo‐1,4‐dihydronaphthalen‐2‐yl)
benzamideꢀ (3r).ꢀ Hꢀ NMRꢀ (400ꢀ MHz,ꢀ CDCl
1H),ꢀ8.06–8.00ꢀ(m,ꢀ1H),ꢀ7.77–7.69ꢀ(m,ꢀ2H),ꢀ7.58–7.52ꢀ(m,ꢀ1H),ꢀ
7.52–7.43ꢀ(m,ꢀ2H),ꢀ7.37ꢀ(dd,ꢀJꢀ=ꢀ7.4,ꢀ1.3ꢀHz,ꢀ1H),ꢀ6.98ꢀ(s,ꢀ1H),ꢀ
6.03ꢀ(s,ꢀ1H),ꢀ1.36ꢀ(s,ꢀ9H).ꢀ CꢀNMRꢀ(100ꢀMHz,ꢀCDCl )ꢀδꢀ185.2,ꢀ
184.0,ꢀ 168.7,ꢀ 151.4,ꢀ 138.1,ꢀ 133.8,ꢀ 133.7,ꢀ 133.0,ꢀ 132.7,ꢀ 130.8,ꢀ
130.5,ꢀ129.8,ꢀ126.8,ꢀ126.5,ꢀ126.3,ꢀ52.0,ꢀ28.8.ꢀTwoꢀcarbonsꢀareꢀ
1
7
8
.50ꢀ(d,ꢀJꢀ=ꢀ2.0ꢀHz,ꢀ1H),ꢀ7.47ꢀ(dd,ꢀJꢀ=ꢀ8.1,ꢀ2.1ꢀHz,ꢀ1H),ꢀ7.23ꢀ(d,ꢀJꢀ=ꢀ
.1ꢀHz,ꢀ1H),ꢀ6.81ꢀ(s,ꢀ2H),ꢀ6.74ꢀ(s,ꢀ1H),ꢀ5.96ꢀ(s,ꢀ1H),ꢀ1.38ꢀ(s,ꢀ9H).ꢀ
)ꢀδꢀ187.3,ꢀ185.6,ꢀ167.2,ꢀ148.2,ꢀ139.2,ꢀ
37.1,ꢀ137.0,ꢀ135.9,ꢀ131.7,ꢀ131.7,ꢀ131.5,ꢀ130.9,ꢀ127.0,ꢀ52.4,ꢀ28.7.ꢀ
3
)ꢀ δꢀ 8.14–8.08ꢀ (m,ꢀ
13CꢀNMRꢀ(100ꢀMHz,ꢀCDCl
3
13
1
3
+
HRMS:ꢀ [Mꢀ +ꢀ H] ꢀ calculatedꢀ forꢀ C17
3
H17ClNO :ꢀ 318.0897,ꢀ foundꢀ
3
18.0897.ꢀ
+
N‐(tert‐butyl)‐6‐chloro‐2',5'‐dioxo‐2',5'‐dihydro‐[1,1'‐
notꢀvisibleꢀdueꢀtoꢀoverlappingꢀpeaks.ꢀHRMS:ꢀ[Mꢀ+ꢀH] ꢀcalculatedꢀ
1
biphenyl]‐2‐carboxamideꢀ (3l’).ꢀ Hꢀ NMRꢀ (400ꢀ MHz,ꢀ CDCl
3
)ꢀ δꢀ
forꢀC21H20NO :ꢀ334.1443,ꢀfoundꢀ334.1440.ꢀ
3
7
.53ꢀ(d,ꢀJꢀ=ꢀ7.8ꢀHz,ꢀ1H),ꢀ7.44–7.35ꢀ(m,ꢀ2H),ꢀ6.90–6.82ꢀ(m,ꢀ2H),ꢀ
N‐(tert‐butyl)‐3',4'‐dimethyl‐2',5'‐dioxo‐2',5'‐dihydro‐[1,1'‐
13
1
6
.74ꢀ(d,ꢀJꢀ=ꢀ2.0ꢀHz,ꢀ1H),ꢀ5.68ꢀ(s,ꢀ1H),ꢀ1.31ꢀ(s,ꢀ9H).ꢀ CꢀNMRꢀ(100ꢀ
)ꢀδꢀ 187.0,ꢀ 185.7,ꢀ 167.1,ꢀ145.5,ꢀ139.7,ꢀ 137.1,ꢀ136.8,ꢀ
34.7,ꢀ134.3,ꢀ131.5,ꢀ130.9,ꢀ130.4,ꢀ125.1,ꢀ52.3,ꢀ28.7.ꢀHRMS:ꢀ[Mꢀ+ꢀ
biphenyl]‐2‐carboxamideꢀ (3s).ꢀ Hꢀ NMRꢀ (400ꢀ MHz,ꢀ CDCl
3
)ꢀ δꢀ
MHz,ꢀ CDCl
1
3
7.53–7.40ꢀ(m,ꢀ3H),ꢀ7.31–7.27ꢀ(m,ꢀ1H),ꢀ6.71ꢀ(s,ꢀ1H),ꢀ5.98ꢀ(s,ꢀ1H),ꢀ
2.06ꢀ (s,ꢀ 3H),ꢀ 2.04ꢀ (s,ꢀ 3H),ꢀ 1.39ꢀ (s,ꢀ 9H).ꢀ 13Cꢀ NMRꢀ (100ꢀ MHz,ꢀ
+
H] ꢀcalculatedꢀforꢀC17
3
H17ClNO :ꢀ318.0897,ꢀfoundꢀ318.0899.ꢀ
CDCl )ꢀδꢀ187.5,ꢀ186.2,ꢀ168.7,ꢀ149.0,ꢀ141.5,ꢀ141.3,ꢀ137.8,ꢀ133.7,ꢀ
3
N‐(tert‐butyl)‐6‐fluoro‐2',5'‐dioxo‐2',5'‐dihydro‐[1,1'‐
131.1,ꢀ130.8,ꢀ130.4,ꢀ129.6,ꢀ126.5,ꢀ52.0,ꢀ28.8,ꢀ12.7,ꢀ12.4.ꢀHRMS:ꢀ
ꢀ
1
+
biphenyl]‐2‐carboxamideꢀ (3m). Hꢀ NMRꢀ (400ꢀ MHz,ꢀ CDCl
3
)ꢀ δꢀ
[Mꢀ+ꢀH] ꢀcalculatedꢀforꢀC19
H
22NO :ꢀ312.1600,ꢀfoundꢀ312.1605.ꢀ
3
7
8
.42ꢀ(td,ꢀJꢀ=ꢀ8.0,ꢀ5.3ꢀHz,ꢀ1H),ꢀ7.33ꢀ(d,ꢀJꢀ=ꢀ7.2ꢀHz,ꢀ1H),ꢀ7.24ꢀ(t,ꢀJꢀ=ꢀ
N‐(tert‐butyl)‐4'‐methyl‐2',5'‐dioxo‐2',5'‐dihydro‐[1,1'‐
biphenyl]‐2‐carboxamideꢀ andꢀ N‐(tert‐butyl)‐3'‐methyl‐2',5'‐
dioxo‐2',5'‐dihydro‐[1,1'‐biphenyl]‐2‐carboxamideꢀ (3t).ꢀ Se‐
13
.8ꢀ Hz,ꢀ 1H),ꢀ 6.87–6.79ꢀ (m,ꢀ 3H),ꢀ 5.89ꢀ (s,ꢀ 1H),ꢀ 1.36ꢀ (s,ꢀ 9H).ꢀ Cꢀ
)ꢀ δꢀ 187.1,ꢀ 185.4,ꢀ 167.2ꢀ (d,ꢀ Jꢀ =ꢀ 2.7ꢀ Hz),ꢀ
60.1ꢀ(d,ꢀJꢀ=ꢀ248.7ꢀHz),ꢀ141.8,ꢀ139.7ꢀ(d,ꢀJꢀ=ꢀ1.7ꢀHz),ꢀ137.1,ꢀ137.0,ꢀ
ꢀ
NMRꢀ (100ꢀ MHz,ꢀ CDCl
3
1
1
1
1
lectedꢀsignals:ꢀMajor:ꢀ HꢀNMRꢀ(400ꢀMHz,ꢀCDCl
3
)ꢀδꢀ7.54–7.41ꢀ(m,ꢀ
34.4ꢀ(d,ꢀJꢀ=ꢀ3.0ꢀHz),ꢀ131.0ꢀ(d,ꢀJꢀ=ꢀ8.7ꢀHz),ꢀ122.4ꢀ(d,ꢀJꢀ=ꢀ3.4ꢀHz),ꢀ
20.2ꢀ(d,ꢀJꢀ=ꢀ15.7ꢀHz),ꢀ118.2ꢀ(d,ꢀJꢀ=ꢀ22.9ꢀHz),ꢀ52.2,ꢀ28.7.ꢀHRMS:ꢀ
3H),ꢀ7.30–7.26ꢀ (m,ꢀ1H),ꢀ6.01ꢀ(s,ꢀ1H),ꢀ2.06ꢀ(d,ꢀ Jꢀ=ꢀ1.5ꢀHz,ꢀ3H),ꢀ
13
1.39ꢀ(s,ꢀ9H).ꢀ CꢀNMRꢀ(100ꢀMHz,ꢀCDCl )ꢀδꢀ187.6,ꢀ186.5,ꢀ168.6,ꢀ
3
+
[Mꢀ+ꢀH] ꢀcalculatedꢀforꢀC17
3
H17FNO :ꢀ302.1192,ꢀfoundꢀ302.1196.ꢀ
149.6,ꢀ 146.4,ꢀ 137.6,ꢀ 133.7,ꢀ 131.3,ꢀ 130.9,ꢀ 130.4,ꢀ 129.7,ꢀ 126.5,ꢀ
1
N‐(tert‐butyl)‐3‐methoxy‐2',5'‐dioxo‐2',5'‐dihydro‐[1,1'‐
52.0,ꢀ28.7,ꢀ16.2.ꢀMinor:ꢀ HꢀNMRꢀ(400ꢀMHz,ꢀCDCl
3
)ꢀδꢀ7.54–7.41ꢀ
1
biphenyl]‐2‐carboxamideꢀ (3n).ꢀ Hꢀ NMRꢀ (400ꢀ MHz,ꢀ CDCl
3
)ꢀ δꢀ
(m,ꢀ3H),ꢀ7.30–7.26ꢀ(m,ꢀ1H),ꢀ6.00ꢀ(s,ꢀ1H),ꢀ2.09ꢀ(d,ꢀJꢀ=ꢀ1.5ꢀHz,ꢀ3H),ꢀ
13
7.45–7.37ꢀ(m,ꢀ1H),ꢀ7.05ꢀ(d,ꢀJꢀ=ꢀ8.4ꢀHz,ꢀ1H),ꢀ6.96ꢀ(s,ꢀ1H),ꢀ6.89ꢀ(d,ꢀJꢀ
=ꢀ7.6ꢀHz,ꢀ1H),ꢀ6.81–6.78ꢀ(m,ꢀ2H),ꢀ6.67ꢀ(d,ꢀJꢀ=ꢀ2.1ꢀHz,ꢀ1H),ꢀ3.92ꢀ(s,ꢀ
H),ꢀ 1.36ꢀ (s,ꢀ 9H).ꢀ 13Cꢀ NMRꢀ (100ꢀ MHz,ꢀ CDCl
3 )ꢀ δꢀ 187.8,ꢀ 185.5,ꢀ
1.39ꢀ(s,ꢀ9H).ꢀ CꢀNMRꢀ(100ꢀMHz,ꢀCDCl )ꢀδꢀ188.1,ꢀ186.1,ꢀ168.6,ꢀ
3
149.3,ꢀ146.4,ꢀ137.8,ꢀ133.1,ꢀ131.5,ꢀ130.8,ꢀ130.5,ꢀ126.5,ꢀ52.0,ꢀ28.7,ꢀ
+
3
15.8.ꢀHRMS:ꢀ[Mꢀ+ꢀH] ꢀcalculatedꢀforꢀC18
H
20NO :ꢀ298.1443,ꢀfoundꢀ
3

ꢀ
ZisongꢀQiꢀetꢀal.ꢀ/ꢀChineseꢀJournalꢀofꢀCatalysisꢀ36ꢀ(2015)ꢀ48–56ꢀ
51ꢀ
2
98.1447.ꢀ
Hz,ꢀ1H),ꢀ6.02ꢀ(d,ꢀJꢀ=ꢀ7.0ꢀHz,ꢀ1H),ꢀ4.12–4.00ꢀ(m,ꢀ1H),ꢀ1.21ꢀ(d,ꢀJꢀ=ꢀ
13
N‐(tert‐butyl)‐4'‐methoxy‐2',5'‐dioxo‐2',5'‐dihydro‐[1,1'‐
6.6ꢀHz,ꢀ6H).ꢀ CꢀNMRꢀ(100ꢀMHz,ꢀCDCl )ꢀδꢀ187.6,ꢀ185.9,ꢀ168.0,ꢀ
3
biphenyl]‐2‐carboxamideꢀ andꢀ N‐(tert‐butyl)‐3'‐methoxy‐2',5'‐
dioxo‐2',5'‐dihydro‐[1,1'‐biphenyl]‐2‐carboxamideꢀ (3u).ꢀ Se‐
ꢀ
149.4,ꢀ 137.1,ꢀ 136.9,ꢀ 136.5,ꢀ 133.4,ꢀ 131.5,ꢀ 131.1,ꢀ 130.5,ꢀ 129.9,ꢀ
+
126.6,ꢀ 42.3,ꢀ 22.8.ꢀ HRMS:ꢀ [Mꢀ +ꢀ H] ꢀ calculatedꢀ forꢀ C16
H
16NO :ꢀ
3
1
lectedꢀsignals:ꢀMajor:ꢀ HꢀNMRꢀ(400ꢀMHz,ꢀCDCl
3
)ꢀδꢀ7.55–7.41ꢀ(m,ꢀ
270.1130,ꢀfoundꢀ270.1134.ꢀ
3
1
1
1
H),ꢀ7.28ꢀ(t,ꢀJꢀ=ꢀ6.2ꢀHz,ꢀ1H),ꢀ6.70ꢀ(s,ꢀ1H),ꢀ6.05ꢀ(s,ꢀ1H),ꢀ5.97ꢀ(s,ꢀ
N‐cyclohexyl‐2',5'‐dioxo‐2',5'‐dihydro‐[1,1'‐biphenyl]‐2‐
H),ꢀ 3.84ꢀ (s,ꢀ 3H),ꢀ 1.40ꢀ (s,ꢀ 9H).ꢀ 13Cꢀ NMRꢀ (100ꢀ MHz,ꢀ CDCl
1
3
)ꢀ δꢀ
3
carboxamideꢀ(3ca).ꢀ HꢀNMRꢀ(400ꢀMHz,ꢀCDCl )ꢀδꢀ7.58–7.45ꢀ(m,ꢀ
85.8,ꢀ 182.1,ꢀ 168.4,ꢀ 159.1,ꢀ 150.0,ꢀ 137.9,ꢀ 133.1,ꢀ 130.7,ꢀ 130.4,ꢀ
3H),ꢀ7.30ꢀ(d,ꢀJꢀ=ꢀ7.5ꢀHz,ꢀ1H),ꢀ6.86–6.78ꢀ(m,ꢀ2H),ꢀ6.74ꢀ(d,ꢀJꢀ=ꢀ2.0ꢀ
Hz,ꢀ1H),ꢀ5.99ꢀ(d,ꢀJꢀ=ꢀ7.5ꢀHz,ꢀ1H),ꢀ3.82–3.71ꢀ(m,ꢀ1H),ꢀ2.01–1.91ꢀ
(m,ꢀ2H),ꢀ1.79–1.69ꢀ(m,ꢀ2H),ꢀ1.63ꢀ(d,ꢀJꢀ=ꢀ10.6ꢀHz,ꢀ2H),ꢀ1.45–1.31ꢀ
1
29.8,ꢀ129.4,ꢀ126.5,ꢀ107.8,ꢀ56.3,ꢀ51.9,ꢀ28.7.ꢀMinor:ꢀ HꢀNMRꢀ(400ꢀ
MHz,ꢀCDCl
3
)ꢀδꢀ7.55–7.41ꢀ(m,ꢀ3H),ꢀ7.28ꢀ(t,ꢀJꢀ=ꢀ6.2ꢀHz,ꢀ1H),ꢀ6.65ꢀ(d,ꢀ
13
Jꢀ=ꢀ2.3ꢀHz,ꢀ1H),ꢀ6.05ꢀ(s,ꢀ1H),ꢀ5.96ꢀ(d,ꢀJꢀ=ꢀ2.3ꢀHz,ꢀ1H),ꢀ3.82ꢀ(s,ꢀ3H),ꢀ
(m,ꢀ2H),ꢀ1.27–1.16ꢀ(m,ꢀ2H).ꢀ CꢀNMRꢀ(100ꢀMHz,ꢀCDCl )ꢀδꢀ187.6,ꢀ
3
13
1
1
5
3
.38ꢀ(s,ꢀ9H).ꢀ CꢀNMRꢀ(100ꢀMHz,ꢀCDCl
59.4,ꢀ 147.5,ꢀ 137.4,ꢀ 131.9,ꢀ 130.8,ꢀ 130.4,ꢀ 129.7,ꢀ 126.5,ꢀ 107.7,ꢀ
6.4,ꢀ 52.0,ꢀ 28.7.ꢀ HRMS:ꢀ [Mꢀ +ꢀ H] ꢀ calculatedꢀ forꢀ C18
14.1392,ꢀfoundꢀ314.1395.ꢀ
3
)ꢀδꢀ187.3,ꢀ180.6,ꢀ171.2,ꢀ
185.9,ꢀ 167.9,ꢀ 149.5,ꢀ 137.2,ꢀ 136.9,ꢀ 136.6,ꢀ 133.4,ꢀ 131.5,ꢀ 131.1,ꢀ
+
130.5,ꢀ129.9,ꢀ126.6,ꢀ49.1,ꢀ33.2,ꢀ25.7,ꢀ25.0.ꢀHRMS:ꢀ[Mꢀ+ꢀH] ꢀcal‐
+
4
H20NO :ꢀ
culatedꢀforꢀC19
H
20NO :ꢀ310.1443,ꢀfoundꢀ310.1445.ꢀ
3
N‐(1‐adamantanyl)‐2',5'‐dioxo‐2',5'‐dihydro‐[1,1'‐biphenyl]‐
1
N‐(tert‐butyl)‐4'‐chloro‐2',5'‐dioxo‐2',5'‐dihydro‐[1,1'‐
biphenyl]‐2‐carboxamideꢀ andꢀ N‐(tert‐butyl)‐3'‐chloro‐2',5'‐
dioxo‐2',5'‐dihydro‐[1,1'‐biphenyl]‐2‐carboxamideꢀ (3v).ꢀ Se‐
2‐carboxamideꢀ (3da).ꢀ Hꢀ NMRꢀ (400ꢀ MHz,ꢀ CDCl
3
)ꢀ δꢀ 7.56–7.42ꢀ
ꢀ
(m,ꢀ3H),ꢀ7.31–7.26ꢀ(m,ꢀ1H),ꢀ6.86–6.78ꢀ(m,ꢀ2H),ꢀ6.74ꢀ(d,ꢀJꢀ=ꢀ2.0ꢀ
Hz,ꢀ1H),ꢀ5.84ꢀ(s,ꢀ1H),ꢀ2.09ꢀ(s,ꢀ3H),ꢀ2.03ꢀ(d,ꢀJꢀ=ꢀ2.6ꢀHz,ꢀ6H),ꢀ1.69ꢀ
1
1
13
lectedꢀ Hꢀ NMRꢀ signals:ꢀ 1)ꢀ Hꢀ NMRꢀ (400ꢀ MHz,ꢀ CDCl
3
)ꢀ δꢀ
(s,ꢀ6H).ꢀ CꢀNMRꢀ(100ꢀMHz,ꢀCDCl
3
)ꢀδꢀ187.6,ꢀ185.8,ꢀ168.2,ꢀ149.6,ꢀ
7
2
.55–7.45ꢀ(m,ꢀ3H),ꢀ7.32–7.27ꢀ(m,ꢀ1H),ꢀ6.05ꢀ(s,ꢀ1H),ꢀ1.39ꢀ(s,ꢀ9H).ꢀ
137.8,ꢀ 137.1,ꢀ 137.1,ꢀ 133.2,ꢀ 131.3,ꢀ 130.9,ꢀ 130.5,ꢀ 129.9,ꢀ 126.5,ꢀ
1
+
)ꢀ HꢀNMRꢀ(400ꢀ MHz,ꢀ CDCl
3
)ꢀ δꢀ 7.55–7.45ꢀ (m,ꢀ 3H),ꢀ 7.32–7.27ꢀ
52.8,ꢀ41.6,ꢀ36.5,ꢀ29.6.ꢀHRMS:ꢀ[Mꢀ+ꢀH] ꢀcalculatedꢀforꢀC23
H
24NO :ꢀ
3
13
(m,ꢀ1H),ꢀ6.05ꢀ(s,ꢀ1H),ꢀ1.39ꢀ(s,ꢀ9H).ꢀ CꢀNMRꢀ(100ꢀMHz,ꢀCDCl
3
)ꢀδꢀ
362.1756,ꢀfoundꢀ362.1761.ꢀ
1
1
1
1
5
3
85.10,ꢀ183.62,ꢀ179.75,ꢀ178.53,ꢀ168.40,ꢀ168.28,ꢀ150.29,ꢀ149.84,ꢀ
44.64,ꢀ144.45,ꢀ137.68,ꢀ137.50,ꢀ134.20,ꢀ134.07,ꢀ133.15,ꢀ132.68,ꢀ
31.08,ꢀ131.00,ꢀ130.54,ꢀ130.33,ꢀ130.20,ꢀ126.49,ꢀ126.47,ꢀ52.28,ꢀ
2.15,ꢀ28.77,ꢀ28.76.ꢀHRMS:ꢀ[Mꢀ+ꢀH] ꢀcalculatedꢀforꢀC17
2‐Hydroxy‐6H‐benzo[c]chromen‐6‐oneꢀ (4a).ꢀ Hꢀ NMRꢀ (400ꢀ
MHz,ꢀDMSO‐d )ꢀδꢀ9.73ꢀ(s,ꢀ1H),ꢀ8.33–8.21ꢀ(m,ꢀ2H),ꢀ7.98–7.91ꢀ(m,ꢀ
6
1H),ꢀ7.72–7.66ꢀ(m,ꢀ1H),ꢀ7.62ꢀ(d,ꢀJꢀ=ꢀ2.7ꢀHz,ꢀ1H),ꢀ7.28ꢀ(d,ꢀJꢀ=ꢀ8.9ꢀ
Hz,ꢀ 1H),ꢀ 7.02ꢀ (dd,ꢀ Jꢀ =ꢀ 8.9,ꢀ 2.8ꢀ Hz,ꢀ 1H).ꢀ 13Cꢀ NMRꢀ (100ꢀ MHz,ꢀ
+
H
17ClNO :ꢀ
3
18.0897,ꢀfoundꢀ318.0903.ꢀ
DMSO‐d
6
)ꢀ δꢀ 160.9,ꢀ 154.7,ꢀ 144.4,ꢀ 135.7,ꢀ 134.7,ꢀ 130.2,ꢀ 129.7,ꢀ
+
N‐(tert‐butyl)‐2',5'‐dioxo‐2',5'‐dihydro‐[1,1':4',1''‐terphenyl]‐
‐carboxamideꢀ andꢀ N‐(tert‐butyl)‐2',5'‐dioxo‐2',5'‐dihydro‐
122.9,ꢀ121.1,ꢀ118.9,ꢀ118.7,ꢀ118.6,ꢀ108.7.ꢀHRMS:ꢀ[Mꢀ+ꢀH] ꢀcalcu‐
2
ꢀ
latedꢀforꢀC13
2‐Hydroxy‐8‐methyl‐6H‐benzo[c]chromen‐6‐oneꢀ (4b).ꢀ 1Hꢀ
NMRꢀ (400ꢀ MHz,ꢀ DMSO‐d )ꢀ δꢀ 9.69ꢀ (s,ꢀ 1H),ꢀ 8.15ꢀ (d,ꢀ Jꢀ=ꢀ8.1ꢀHz,ꢀ
9 3
H O :ꢀ213.0555,ꢀfoundꢀ213.0552.ꢀ
[1,1':3',1''‐terphenyl]‐2‐carboxamideꢀ (3w).ꢀ Selectedꢀ signals:ꢀ
1
Major:ꢀ HꢀNMRꢀ(400ꢀMHz,ꢀCDCl
3
)ꢀδꢀ6.85ꢀ(d,ꢀJꢀ=ꢀ2.6ꢀHz,ꢀ1H),ꢀ6.75ꢀ
6
13
(d,ꢀJꢀ=ꢀ2.6ꢀHz,ꢀ1H),ꢀ6.11ꢀ(s,ꢀ1H),ꢀ1.32ꢀ(s,ꢀ9H).ꢀ CꢀNMRꢀ(100ꢀMHz,ꢀ
1H),ꢀ8.04ꢀ(s,ꢀ1H),ꢀ7.74ꢀ(d,ꢀJꢀ=ꢀ8.1ꢀHz,ꢀ1H),ꢀ7.56ꢀ(d,ꢀJꢀ=ꢀ2.3ꢀHz,ꢀ1H),ꢀ
7.25ꢀ(d,ꢀJꢀ=ꢀ8.8ꢀHz,ꢀ1H),ꢀ6.97ꢀ(dd,ꢀJꢀ=ꢀ8.8,ꢀ2.5ꢀHz,ꢀ1H),ꢀ2.46ꢀ(s,ꢀ3H).ꢀ
CDCl )ꢀδꢀ187.6,ꢀ185.4,ꢀ168.1,ꢀ150.2,ꢀ146.8,ꢀ137.1,ꢀ133.9,ꢀ133.4,ꢀ
3
1
32.8,ꢀ 131.0,ꢀ 130.9,ꢀ 130.7,ꢀ 129.8,ꢀ 129.7,ꢀ 129.4,ꢀ 128.2,ꢀ 126.6,ꢀ
13Cꢀ NMRꢀ (100ꢀ MHz,ꢀ DMSO‐d
)ꢀ δꢀ 160.9,ꢀ 154.7,ꢀ 144.1,ꢀ 139.6,ꢀ
136.7,ꢀ 132.2,ꢀ 129.9,ꢀ 122.9,ꢀ 120.9,ꢀ 118.8,ꢀ 118.46,ꢀ 118.4,ꢀ 108.4,ꢀ
6
1
5
1.9,ꢀ28.7.ꢀMinor:ꢀ HꢀNMRꢀ(400ꢀMHz,ꢀCDCl
3
)ꢀδꢀ6.89ꢀ(s,ꢀ1H),ꢀ6.82ꢀ
)ꢀδꢀ
86.9,ꢀ 186.0,ꢀ 168.5,ꢀ 148.9,ꢀ 146.2,ꢀ 137.8,ꢀ 133.1,ꢀ 132.9,ꢀ 132.7,ꢀ
13
+
(s,ꢀ1H),ꢀ6.09ꢀ(s,ꢀ1H),ꢀ1.39ꢀ(s,ꢀ9H).ꢀ CꢀNMRꢀ(100ꢀMHz,ꢀCDCl
3
21.2.ꢀHRMS:ꢀ[Mꢀ+ꢀH] ꢀcalculatedꢀforꢀC14
H
11
O :ꢀ227.0708,ꢀfoundꢀ
3
1
1
227.0706.ꢀ
31.8,ꢀ130.5,ꢀ130.0,ꢀ129.5,ꢀ128.5,ꢀ126.52ꢀ51.9,ꢀ28.7.ꢀHRMS:ꢀ[Mꢀ+ꢀ
9‐Chloro‐2‐hydroxy‐6H‐benzo[c]chromen‐6‐oneꢀ (4c).ꢀ 1Hꢀ
NMRꢀ (400ꢀ MHz,ꢀ DMSO‐d )ꢀ δꢀ 9.74ꢀ (s,ꢀ 1H),ꢀ 8.38ꢀ (d,ꢀ Jꢀ=ꢀ1.9ꢀHz,ꢀ
+
H] ꢀcalculatedꢀforꢀC23
3
H22NO :ꢀ360.1600,ꢀfoundꢀ360.1600.ꢀ
6
N‐(tert‐butyl)‐2‐(3,6‐dioxocyclohexa‐1,4‐dien‐1‐yl)cyclopent‐
1H),ꢀ8.22ꢀ(d,ꢀJꢀ=ꢀ8.5ꢀHz,ꢀ1H),ꢀ7.70ꢀ(dd,ꢀJꢀ=ꢀ8.5,ꢀ1.9ꢀHz,ꢀ1H),ꢀ7.65ꢀ
(d,ꢀJꢀ=ꢀ2.7ꢀHz,ꢀ1H),ꢀ7.27ꢀ(d,ꢀJꢀ=ꢀ8.9ꢀHz,ꢀ1H),ꢀ7.04ꢀ(dd,ꢀJꢀ=ꢀ8.9,ꢀ2.7ꢀ
1
1
1
1
9
1
3
‐enecarboxamideꢀ(3x).ꢀ HꢀNMRꢀ(400ꢀMHz,ꢀCDCl )ꢀδꢀ6.82ꢀ(d,ꢀJꢀ=ꢀ
13
0.2ꢀHz,ꢀ1H),ꢀ6.73ꢀ(dd,ꢀJꢀ=ꢀ10.2,ꢀ2.5ꢀHz,ꢀ1H),ꢀ6.55ꢀ(d,ꢀJꢀ=ꢀ2.5ꢀHz,ꢀ
Hz,ꢀ1H).ꢀ CꢀNMRꢀ(100ꢀMHz,ꢀDMSO‐d )ꢀ δꢀ160.2,ꢀ154.8,ꢀ144.8,ꢀ
6
H),ꢀ5.36ꢀ(s,ꢀ1H),ꢀ2.76–2.66ꢀ(m,ꢀ4H),ꢀ2.11–2.02ꢀ(m,ꢀ2H),ꢀ1.31ꢀ(s,ꢀ
141.1,ꢀ 136.6,ꢀ 132.4,ꢀ 129.8,ꢀ 122.89,ꢀ 119.9,ꢀ 119.6,ꢀ 118.6,ꢀ 117.8,ꢀ
H).ꢀ 13Cꢀ NMRꢀ (100ꢀ MHz,ꢀ CDCl
3
)ꢀ δꢀ 187.4,ꢀ 185.0,ꢀ 164.8,ꢀ 146.4,ꢀ
109.2.ꢀ HRMS:ꢀ [Mꢀ +ꢀ H] ꢀ calculatedꢀ forꢀ C13
+
H
ClO :ꢀ 247.0162,ꢀ
8
3
40.5,ꢀ 139.9,ꢀ 137.6,ꢀ 136.5,ꢀ 130.7,ꢀ 51.6,ꢀ 38.2,ꢀ 34.9,ꢀ 28.9,ꢀ 22.6.ꢀ
foundꢀ247.0161.ꢀ
+
9‐Bromo‐2‐hydroxy‐6H‐benzo[c]chromen‐6‐oneꢀ (4d).ꢀ 1Hꢀ
NMRꢀ(400ꢀMHz,ꢀDMSO‐d )ꢀδꢀ9.73ꢀ(d,ꢀJꢀ=ꢀ3.8ꢀHz,ꢀ1H),ꢀ8.48ꢀ(d,ꢀJꢀ=ꢀ
HRMS:ꢀ [Mꢀ +ꢀ H] ꢀ calculatedꢀ forꢀ C16
H
20NO :ꢀ 274.1443,ꢀ foundꢀ
3
274.1446.ꢀ
6
2
2
N ,N ''‐di‐tert‐butyl‐2',5'‐dioxo‐2',5'‐dihydro‐[1,1':3',1''‐
11.4ꢀHz,ꢀ 1H),ꢀ8.12ꢀ (t,ꢀJꢀ=ꢀ8.0ꢀHz,ꢀ1H),ꢀ7.82ꢀ(t,ꢀJꢀ=ꢀ7.9ꢀHz,ꢀ1H),ꢀ
7.69–7.59ꢀ(m,ꢀ1H),ꢀ7.26ꢀ(dd,ꢀJꢀ=ꢀ8.6,ꢀ6.9ꢀHz,ꢀ1H),ꢀ7.04ꢀ(dt,ꢀJꢀ=ꢀ8.8,ꢀ
1
terphenyl]‐2,2''‐dicarboxamideꢀ (3aa).ꢀ Hꢀ NMRꢀ (400ꢀ MHz,ꢀ
CDCl
13
3
)ꢀ δꢀ 7.56–7.52ꢀ (m,ꢀ 2H),ꢀ 7.49–7.40ꢀ (m,ꢀ 6H),ꢀ 6.80ꢀ (s,ꢀ 2H),ꢀ
3.2ꢀHz,ꢀ1H).ꢀ CꢀNMRꢀ(100ꢀMHz,ꢀDMSO‐d )ꢀδꢀ160.4,ꢀ154.8,ꢀ144.7,ꢀ
6
13
6
1
1
4
.04ꢀ(s,ꢀ2H),ꢀ1.21ꢀ(s,ꢀ9H).ꢀ CꢀNMRꢀ(100ꢀMHz,ꢀCDCl
85.4,ꢀ 168.4,ꢀ 148.7,ꢀ 137.8,ꢀ 132.3,ꢀ 132.2,ꢀ 130.4,ꢀ 130.2,ꢀ 129.6,ꢀ
27.3,ꢀ 52.1,ꢀ 28.7.ꢀ HRMS:ꢀ [Mꢀ +ꢀ H] ꢀ calculatedꢀ forꢀ C28
59.2284,ꢀfoundꢀ459.2288.ꢀ
3
)ꢀδꢀ187.2,ꢀ
136.6,ꢀ 132.6,ꢀ 132.2,ꢀ 130.3,ꢀ 125.8,ꢀ 120.2,ꢀ 119.6,ꢀ 118.6,ꢀ 117.6,ꢀ
+
109.2.ꢀ HRMS:ꢀ [Mꢀ +ꢀ H] ꢀ calculatedꢀ forꢀ C13
H
8
BrO :ꢀ 290.9657,ꢀ
3
+
31 2 4
H N O :ꢀ
foundꢀ290.9659.ꢀ
N‐isopropyl‐2',5'‐dioxo‐2',5'‐dihydro‐[1,1'‐biphenyl]‐2‐
3.ꢀ ꢀ Resultsꢀandꢀdiscussionꢀ
1
3
carboxamideꢀ(3ba).ꢀ HꢀNMRꢀ(400ꢀMHz,ꢀCDCl )ꢀδꢀ7.57–7.43ꢀ(m,ꢀ
3H),ꢀ7.30ꢀ(d,ꢀJꢀ=ꢀ7.2ꢀHz,ꢀ1H),ꢀ6.84–6.77ꢀ(m,ꢀ2H),ꢀ6.74ꢀ(d,ꢀJꢀ=ꢀ1.8ꢀ
TheꢀreactionꢀofꢀN‐(tert‐butyl)benzamideꢀ1aꢀandꢀ1,4‐benzo‐
ꢀ

52ꢀ
ZisongꢀQiꢀetꢀal.ꢀ/ꢀChineseꢀJournalꢀofꢀCatalysisꢀ36ꢀ(2015)ꢀ48–56ꢀ
quinoneꢀ2aꢀwasꢀselectedꢀasꢀaꢀmodelꢀforꢀscreeningꢀofꢀtheꢀreac‐
tionꢀparametersꢀ(Tableꢀ1).ꢀWeꢀinitiallyꢀperformedꢀthisꢀreactionꢀ
inꢀ theꢀ absenceꢀ ofꢀ anyꢀ externalꢀ oxidantꢀ butꢀ withꢀ 4ꢀ mol%ꢀ ofꢀ
However,ꢀ ortho‐fluoroꢀ substrateꢀ exhibitedꢀ lowerꢀ reactivityꢀ
(3o),ꢀimplyingꢀthatꢀtheꢀelectronicꢀeffectꢀseemsꢀmoreꢀsignificantꢀ
thanꢀtheꢀstericꢀeffectꢀatꢀthisꢀposition.ꢀNotably,ꢀtheꢀreactionsꢀforꢀ
[
RhCp*Cl
productꢀ3aꢀwereꢀdetectedꢀbyꢀGC‐MSꢀ(Tableꢀ1,ꢀentryꢀ1).ꢀWhenꢀ
Cu(OAc) ꢀ(1ꢀequiv)ꢀwasꢀemployedꢀasꢀanꢀoxidant,ꢀ3aꢀwasꢀisolat‐
edꢀinꢀ17%ꢀyieldꢀ(entryꢀ2).ꢀHowever,ꢀnoꢀproductꢀwasꢀobtainedꢀ
whenꢀ AgSbF ꢀ wasꢀ omittedꢀ (entryꢀ 3).ꢀ Withꢀ Ag CO ꢀ orꢀ AgOAcꢀ
beingꢀ anꢀ oxidant,ꢀ theꢀ yieldꢀ ofꢀ 3aꢀ wasꢀ increasedꢀ toꢀ 54%ꢀ andꢀ
1%,ꢀrespectivelyꢀ(entriesꢀ4ꢀandꢀ5).ꢀWeꢀwereꢀpleasedꢀtoꢀfindꢀ
thatꢀ3aꢀwasꢀisolatedꢀinꢀ85%ꢀyieldꢀwhenꢀtheꢀamountꢀofꢀAg CO
2
]
2ꢀandꢀ16ꢀmol%ꢀofꢀAgSbF
6
.ꢀOnlyꢀtracesꢀofꢀtheꢀdesiredꢀ
N‐(tert‐butyl)‐2‐naphthamideꢀ andꢀ N‐(tert‐butyl)thiophene‐2‐
carboxamideꢀ proceededꢀ smoothlyꢀ toꢀ generateꢀ productsꢀ inꢀ
ꢀ
2
moderateꢀyieldsꢀ(3pꢀandꢀ3q).ꢀTheꢀN‐substituentꢀisꢀnotꢀlimitedꢀ
t
toꢀaꢀ Buꢀgroup.ꢀThusꢀbenzamidesꢀbearingꢀN‐alkylꢀgroupsꢀsuchꢀasꢀ
6
2
3
isopropyl,ꢀ cyclohexyl,ꢀ andꢀ adamantylꢀ alsoꢀ underwentꢀ smoothꢀ
couplingꢀ(3ba–3da).ꢀTheꢀscopeꢀofꢀquinoneꢀsubstrateꢀwasꢀnextꢀ
2
investigated.ꢀ Subjectionꢀ ofꢀ 1,4‐naphthoquinoneꢀ andꢀ 2,3‐dime‐
ꢀ
2
3
ꢀ
thyl‐1,4‐benzoquinoneꢀtoꢀtheꢀcouplingꢀwithꢀ1aꢀaffordedꢀ3rꢀandꢀ
3sꢀinꢀ90%ꢀandꢀ64%ꢀyields,ꢀrespectively.ꢀInꢀcontrast,ꢀtheꢀ cou‐
plingꢀ ofꢀ aꢀ mono‐substitutedꢀ quinoneꢀ withꢀ 1aꢀ providedꢀ twoꢀ
regioisomersꢀ inꢀ moderateꢀ totalꢀ yieldsꢀ (3t–3w).ꢀ Furthermore,ꢀ
extensionꢀtoꢀanꢀolefinicꢀsubstrateꢀbearingꢀthisꢀtypeꢀofꢀdirectingꢀ
groupꢀ provedꢀ successful,ꢀ whereꢀ productꢀ 3xꢀ wasꢀ isolatedꢀ inꢀ
52%ꢀyield.ꢀInꢀaddition,ꢀwhenꢀanꢀexcessꢀ(3.0ꢀequiv)ꢀofꢀ1aꢀwasꢀ
used,ꢀ theꢀ diarylationꢀ productꢀ wasꢀ isolatedꢀ asꢀ theꢀ majorꢀ oneꢀ
(3aa).ꢀ ꢀ
wasꢀ increasedꢀ toꢀ 2.0ꢀ equivꢀ (entryꢀ 6).ꢀ Furtherꢀ examinationꢀ ofꢀ
theꢀsolventꢀrevealedꢀthatꢀDCE,ꢀTHF,ꢀdiglyme,ꢀPhCl,ꢀandꢀacetoneꢀ
allꢀ gaveꢀinferiorꢀresultsꢀ (entriesꢀ7–11).ꢀFinally,ꢀtheꢀoptimizedꢀ
conditionsꢀincludeꢀ4ꢀmol%ꢀofꢀ[RhCp*Cl
ofꢀAgSbF ꢀasꢀanꢀadditive,ꢀandꢀ2.0ꢀequivꢀofꢀAg
atꢀ100ꢀ°C.ꢀ
2
]2ꢀasꢀcatalyst,ꢀ16ꢀmol%ꢀ
6
2
CO ꢀinꢀ1,4‐dioxaneꢀ
3
Havingꢀ determinedꢀ theꢀ optimalꢀ conditions,ꢀ weꢀ nextꢀ sur‐
veyedꢀ variousꢀ substratesꢀ toꢀ defineꢀ theꢀ scopeꢀ ofꢀ theꢀ reactionꢀ
(
Tableꢀ2).ꢀN‐(tert‐butyl)benzamidesꢀbearingꢀelectron‐donatingꢀ
ItꢀisꢀnoteworthyꢀthatꢀaꢀC–Hꢀinsertion/lactonizationꢀproductꢀ
4aꢀwasꢀobservedꢀduringꢀtheꢀscreeningꢀstudies.ꢀItꢀhasꢀbeenꢀre‐
portedꢀ thatꢀ theꢀ couplingꢀ ofꢀ benzoicꢀ acidꢀ andꢀ benzoquinoneꢀ
affordedꢀ theꢀ sameꢀ 2‐hydroxy‐6H‐benzo[c]chromen‐6‐oneꢀ un‐
derꢀIr(III)ꢀcatalysis,ꢀhoweverꢀaꢀratherꢀhighꢀcatalystꢀloadingꢀandꢀ
aꢀrelativelyꢀhighꢀtemperatureꢀwereꢀnecessaryꢀtoꢀgiveꢀsyntheti‐
callyꢀusefulꢀyieldsꢀ[91].ꢀEncouragedꢀbyꢀtheseꢀresults,ꢀtheꢀreac‐
tionꢀparametersꢀwereꢀoptimizedꢀforꢀtheꢀsynthesisꢀofꢀ4a.ꢀItꢀwasꢀ
foundꢀ thatꢀ benzamidesꢀ bearingꢀ methylꢀ (4b),ꢀ chloroꢀ (4c),ꢀ andꢀ
bromoꢀ(4d)ꢀgroupsꢀatꢀtheꢀ3‐ꢀorꢀ4‐ꢀpositionꢀunderwentꢀsmoothlyꢀ
couplingꢀ underꢀ theseꢀ redox‐neutralꢀ conditionsꢀ inꢀ acetoneꢀ toꢀ
giveꢀlactonesꢀinꢀmoderateꢀtoꢀgoodꢀyieldsꢀ(Schemeꢀ1).ꢀHowever,ꢀ
weꢀ attemptedꢀ butꢀ failedꢀ toꢀ achieveꢀ thisꢀ typeꢀ reactionꢀ forꢀ
1,4‐naphthoquinone,ꢀwhereꢀonlyꢀquinoneꢀ3rꢀwasꢀisolated.ꢀWeꢀ
notedꢀthatꢀlactonizationꢀviaꢀC–Hꢀactivationꢀofꢀotherꢀamidesꢀhasꢀ
beenꢀreportedꢀ[92–94].ꢀ
groupsꢀatꢀtheꢀpara‐positionꢀgaveꢀtheꢀcorrespondingꢀproductsꢀinꢀ
moderateꢀtoꢀgoodꢀyieldsꢀ(3a–3c,ꢀ3g).ꢀWithꢀaꢀhalogenꢀgroupꢀatꢀ
theꢀ4‐positionꢀofꢀphenylꢀring,ꢀtheꢀarylatedꢀquinonesꢀwereꢀiso‐
latedꢀ inꢀ slightlyꢀ lowerꢀ yieldꢀ (3d–3f).ꢀ However,ꢀ usingꢀ elec‐
tron‐withdrawingꢀgroupsꢀsuchꢀasꢀtrifluoromethylꢀandꢀmethox‐
ycarbonylꢀatꢀtheꢀpara‐positionꢀdecreasedꢀtheꢀyieldꢀofꢀtheꢀprod‐
uctsꢀ (3hꢀandꢀ3i).ꢀ Theꢀ metaꢀ methylꢀ substitutedꢀ substrateꢀ alsoꢀ
gaveꢀ productꢀ inꢀ goodꢀ yieldꢀ (3j)ꢀ andꢀ C–Hꢀ activationꢀ occurredꢀ
selectivelyꢀ atꢀ theꢀ lessꢀ hinderedꢀ position.ꢀ However,ꢀ theꢀ metaꢀ
methoxyꢀ(3kꢀandꢀ3k’)ꢀorꢀchloroꢀ(3lꢀandꢀ3l’)ꢀsubstitutedꢀben‐
zamideꢀ gaveꢀ twoꢀ regio‐isomericꢀproductsꢀthatꢀcouldꢀbeꢀchro‐
matographicallyꢀ separated.ꢀ Inꢀ contrast,ꢀ C–Hꢀ activationꢀ oc‐
curredꢀselectivelyꢀatꢀtheꢀmoreꢀhinderedꢀorthoꢀsiteꢀforꢀtheꢀmetaꢀ
1
13
fluoroꢀsubstitutedꢀbenzamideꢀ(3m),ꢀonꢀtheꢀbasisꢀofꢀ Hꢀandꢀ Cꢀ
NMRꢀanalysis.ꢀortho‐Methoxyꢀsubstitutedꢀbenzamideꢀwasꢀalsoꢀ
effective,ꢀ furnishingꢀ theꢀ arylatedꢀ quinoneꢀ inꢀ 68%ꢀ yieldꢀ (3n).ꢀ
Toꢀprobeꢀtheꢀmechanismꢀofꢀthisꢀdirectꢀarylationꢀofꢀquinones,ꢀ
preliminaryꢀ mechanisticꢀ studiesꢀ wereꢀ carriedꢀ out.ꢀ Aꢀ notableꢀ
Tableꢀ1ꢀ ꢀ
primaryꢀkineticꢀisotopeꢀeffectꢀ(KIE,ꢀk
H
/k ꢀ=ꢀ4.6)ꢀwasꢀobserved,ꢀ
D
CouplingꢀofꢀN‐(tert‐butyl)benzamideꢀwithꢀquinoneꢀunderꢀvariousꢀcon‐
indicatingꢀthatꢀC–Hꢀbondꢀcleavageꢀofꢀ1aꢀisꢀprobablyꢀinvolvedꢀinꢀ
theꢀrate‐limitingꢀstep.ꢀFurthermore,ꢀaꢀcompetitionꢀreactionꢀhasꢀ
beenꢀperformed,ꢀwhereꢀtwoꢀbenzamidesꢀ1bꢀandꢀ1eꢀdifferingꢀinꢀ
ditions.ꢀ
electronicꢀeffectsꢀwereꢀallowedꢀtoꢀcompeteꢀinꢀtheꢀcouplingꢀwithꢀ
1
2
aꢀ(1b:1e:2aꢀ=ꢀ1:1:1ꢀratio).ꢀ HꢀNMRꢀanalysisꢀofꢀtheꢀresultingꢀ
ꢀ
mixtureꢀrevealedꢀthatꢀ3bꢀandꢀ3eꢀwereꢀgeneratedꢀinꢀ2.2:1ꢀratio,ꢀ
suggestingꢀthatꢀcouplingꢀofꢀanꢀelectron‐richꢀareneꢀisꢀfasterꢀthanꢀ
thatꢀofꢀaꢀmoreꢀelectron‐deficientꢀone.ꢀ
Isolatedꢀ
Entryꢀ
Catalystꢀ
Oxidantꢀ(equiv)ꢀ Solventꢀ
yieldꢀ(%)
Traceꢀ
17ꢀ
1
2ꢀ
ꢀ
[RhCp*Cl
[RhCp*Cl
2
]
]
2
/AgSbF
/AgSbF
6
ꢀ
ꢀ
—ꢀ
Dioxaneꢀ
ꢀ(1.0)ꢀ Dioxaneꢀ
ꢀ(1.0)ꢀ Dioxaneꢀ
2
2
6
Cu(OAc)
Cu(OAc)
2
Basedꢀ onꢀ theseꢀ experimentsꢀ andꢀ literatureꢀ precedentsꢀ
3ꢀ
2 2
[RhCp*Cl ] ꢀ
2
ndꢀ
54ꢀ
21ꢀ
85ꢀ
73ꢀ
60ꢀ
Traceꢀ
36ꢀ
41ꢀ
[58,95],ꢀ aꢀ plausibleꢀ mechanismꢀ isꢀ proposedꢀ inꢀ Schemeꢀ 2.ꢀ
4
ꢀ
[RhCp*Cl
[RhCp*Cl
[RhCp*Cl
[RhCp*Cl
[RhCp*Cl
[RhCp*Cl
2
2
2
2
2
2
]
]
]
]
]
]
]
]
2
2
2
2
2
2
2
2
/AgSbF
/AgSbF
/AgSbF
/AgSbF
/AgSbF
/AgSbF
/AgSbF
/AgSbF
6
ꢀ
6
ꢀ
6
ꢀ
6
ꢀ
6
ꢀ
6
ꢀ
6
ꢀ
6
ꢀ
Ag
AgOAcꢀ(1.0)ꢀ Dioxaneꢀ
2 3
CO ꢀ(1.0)ꢀ Dioxaneꢀ
O‐Coordinationꢀ ofꢀ theꢀ amideꢀ toꢀ theꢀ Rh(III)ꢀ centerꢀ andꢀ subse‐
quentꢀ orthoꢀ C–Hꢀ bondꢀ activationꢀ affordedꢀ aꢀ five‐memberedꢀ
rhodacyclicꢀ intermediateꢀ A.ꢀ Insertionꢀ ofꢀ quinoneꢀ 2aꢀ toꢀ Rh–Cꢀ
bondꢀofꢀAꢀgaveꢀaꢀseven‐memberedꢀrhodacycleꢀB,ꢀwhichꢀisꢀfol‐
lowedꢀbyꢀepimerizationꢀatꢀoneꢀofꢀtheꢀ‐positions,ꢀallowingꢀforꢀ
5
ꢀ
6
ꢀ
Ag
2
Ag
2
Ag
2
Ag
2
Ag
2
Ag
2
CO
CO
CO
CO
CO
CO
3
3
3
3
3
3
ꢀ(2.0)ꢀ Dioxaneꢀ
7
ꢀ
ꢀ(2.0)ꢀ
ꢀ(2.0)ꢀ
DCEꢀ
THFꢀ
8
ꢀ
9
ꢀ
ꢀ(2.0)ꢀ Diglymeꢀ
ꢀ(2.0)ꢀ PhClꢀ
ꢀ(2.0)ꢀ Acetoneꢀ
1
1
0ꢀ
1ꢀ
[RhCp*Cl
[RhCp*Cl
2
‐hydrogenꢀeliminationꢀtoꢀprovideꢀtheꢀdesiredꢀproductꢀ3aꢀto‐
2
getherꢀwithꢀtheꢀRh(I)ꢀspeciesꢀ(withꢀeliminationꢀofꢀHX).ꢀTheꢀRh(I)ꢀ
Reactionsꢀ conditions:ꢀ [RhCp*Cl
dant,ꢀ1aꢀ(0.20ꢀmmol),ꢀandꢀ2aꢀ(0.30ꢀmmol)ꢀinꢀsolventꢀ(3ꢀmL)ꢀatꢀ100ꢀ°Cꢀ
]
2 2
ꢀ (4ꢀ mol%),ꢀ AgSbF ꢀ (16ꢀ mol%),ꢀ oxi‐
6
wasꢀ re‐oxidizedꢀ byꢀ Ag
2
CO ꢀ toꢀ regenerateꢀ Rh(III)ꢀ forꢀ theꢀ nextꢀ
3
underꢀnitrogenꢀforꢀ12ꢀh.ꢀ ꢀ
catalyticꢀcycle.ꢀ

ꢀ
ZisongꢀQiꢀetꢀal.ꢀ/ꢀChineseꢀJournalꢀofꢀCatalysisꢀ36ꢀ(2015)ꢀ48–56ꢀ
53ꢀ
Tableꢀ2ꢀ ꢀ
Substrateꢀscope.ꢀ
ꢀ
Isolatedꢀ
yieldꢀ(%)ꢀ
Isolatedꢀ
yieldꢀ(%)ꢀ
Isolatedꢀ
yieldꢀ(%)
Entryꢀ
Productꢀ
Entryꢀ
11ꢀ
Productꢀ
Entry
21ꢀ
Productꢀ
1ꢀ
85ꢀ
27ꢀ
46ꢀ
64ꢀ
3
aꢀ
3kꢀ
3
sꢀ
2ꢀ
80ꢀ
75ꢀ
12ꢀ
13ꢀ
22ꢀ
23ꢀ
73ꢀ
64ꢀ
3
tꢀ
3
bꢀ
3k’ꢀ
(
(
major:minorꢀ=ꢀ2:1)ꢀ
3ꢀ
38ꢀ
36ꢀ
67ꢀ
3
uꢀ
3
cꢀ
3lꢀ
major:minorꢀ=ꢀ6:1)ꢀ
4ꢀ
62ꢀ
66ꢀ
14ꢀ
15ꢀ
24ꢀ
25ꢀ
62ꢀ
70ꢀ
3
vꢀ
3
dꢀ
3l’ꢀ
(1:1)ꢀ
5ꢀ
3
wꢀ
3eꢀ
3mꢀ
(
major:minorꢀ=ꢀ6:1)ꢀ
6
ꢀ
68ꢀ
71ꢀ
52ꢀ
39ꢀ
16ꢀ
17ꢀ
18ꢀ
19ꢀ
68ꢀ
43ꢀ
76ꢀ
65ꢀ
26ꢀ
27ꢀaꢀ
28ꢀ
52ꢀ
49ꢀ
62ꢀ
71ꢀ
3
xꢀ
3
fꢀ
3nꢀ
3oꢀ
7ꢀ
3gꢀ
3aaꢀ
t
NH Bu
O
8ꢀ
O
F3C
O
3hꢀ
3pꢀ
3baꢀ
9ꢀ
29ꢀ
3iꢀ
3qꢀ
3caꢀ
10ꢀ
75ꢀ
20ꢀ
90ꢀ
30ꢀ
77ꢀ
3
jꢀ
3
rꢀ
ꢀ(0.4ꢀmmol),ꢀ1ꢀ(0.20ꢀmmol),ꢀandꢀ2ꢀ(0.30ꢀmmol)ꢀinꢀdioxaneꢀ(3ꢀmL)ꢀatꢀ100ꢀ°Cꢀ
ꢀ(0.8ꢀmmol)ꢀwereꢀused.ꢀ
3daꢀ
Reactionꢀconditions:ꢀ[RhCp*Cl
underꢀnitrogenꢀforꢀ12ꢀh.ꢀ ꢀ1aꢀ(0.6ꢀmmol),ꢀ2aꢀ(0.2ꢀmmol)ꢀandꢀAg
2
]
2
ꢀ(4ꢀmolꢀ%),ꢀAgSbF
6
ꢀ(16ꢀmolꢀ%),ꢀAg
CO
2 3
a
2
CO
3
ꢀ

54ꢀ
ZisongꢀQiꢀetꢀal.ꢀ/ꢀChineseꢀJournalꢀofꢀCatalysisꢀ36ꢀ(2015)ꢀ48–56ꢀ
Schemeꢀ1.ꢀRh(III)‐catalyzedꢀsynthesisꢀofꢀ2‐hydroxy‐6H‐benzo[c]chromen‐6‐ones.
[
[
[
[
[
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.ꢀ ꢀ Conclusionsꢀ
Weꢀ haveꢀ developedꢀ Rh(III)‐catalyzedꢀ C–Hꢀ activationꢀ ofꢀ
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Rh(III)‐catalyzedꢀC–Hꢀactivationꢀofꢀbenzamides:ꢀCouplingꢀwithꢀquinonesꢀ
ꢀ
ZisongꢀQi,ꢀXingweiꢀLi*ꢀ
DalianꢀInstituteꢀofꢀChemicalꢀPhysics,ꢀChineseꢀAcademyꢀofꢀSciencesꢀ
O
NHR
NHR
O
O
O
[Rh(III)]
[
Rh(III)]
Ag CO3
2
+
O
redox-neutral
oxidative
coupling
O
O
O
OH
4
examples
30 examples
ꢀ
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