Catalyst‐Controlled Highly Selective Coupling and Oxygenation of Olefins: A Direct Approach to Alcohols, Ketones, and Diketones

Su, Yijin; Sun, Xiang; Wu, Guosheng; Jiao, Ning

doi:10.1002/anie.201303917

Cited by 188 publications

(83 citation statements)

References 112 publications

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“…725 A radical addition to the styrene is probably a key mechanistic step of this transformation. Oxygen plays multiple roles, as it is involved in the radical formation, serves as an oxidant for reduced catalyst species, and is the reagent that provides the oxygen atoms for the product.…”

Section: Càc and Càheteroatom Bond Forming Additionsmentioning

confidence: 99%

Iron Catalysis in Organic Synthesis

2015

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Section: Càc and Càheteroatom Bond Forming Additionsmentioning

confidence: 99%

Iron Catalysis in Organic Synthesis

2015

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“…Unprotected hydroxyl substituent was tolerant in this reaction and showed good yield (entry 21). N'-Aryl alkanoylhydrazines were also evaluated under optimal conditions (entries [26][27][28][29], the yields were generally good. An exception was 30 N'-phenyl trifluoroacetylhydrazine 1aa for the strong electronwithdrawing ability of CF 3 group.…”

Section: Introductionmentioning

confidence: 99%

Copper(ii)-catalyzed coupling reaction: an efficient and regioselective approach to N′,N′-diaryl acylhydrazines

et al. 2015

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Using N'-aryl acylhydrazines as aryl donors, a novel copper(ii)-catalyzed homo-coupling reaction of N'-aryl acylhydrazines has been developed for the synthesis of N',N'-diaryl acylhydrazines. We also provided a complementary procedure for the preparation of unsymmetrical diaryl acylhydrazines via cross-coupling reaction. These protocols featured mild reaction conditions, wide functional group tolerance and highly regioselective products. Control experiments indicated that this kind of coupling reaction might undergo a transient acyl diazene intermediate.

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“…

The cooperative catalysis of copper,s ilver,a nd Brønsted acid is presented as an ew strategy for olefin functionalization. [7] Some examples of indirect carbohydroxylation of alkenes are known. Synthetically useful functional groups,such as Cl, Br,carbonyl, and chloromethyl, remained intact during the functionalization reaction.

The transition metal catalyzed functionalization of olefins is ap owerful tool to convert readily available petrochemical feedstocks into valuable synthetic building blocks.

…”

mentioning

confidence: 99%

“…[7] Some examples of indirect carbohydroxylation of alkenes are known. However,tothe best of our knowledge,only few papers on direct carbohydroxylation, namely arylhydroxylation of alkenes,h ave been reported, and they involve ar adical process.…”

mentioning

confidence: 99%

Direct Carbohydroxylation of Arylalkenes with Allylic Alcohols: Cooperative Catalysis of Copper, Silver, and a Brønsted Acid

Ahmed

Zhang

et al. 2019

Angewandte Chemie

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The cooperative catalysis of copper,s ilver,a nd Brønsted acid is presented as an ew strategy for olefin functionalization. The catalytic direct carbohydroxylation of arylalkenes with allylic alcohols provided as traightforward and efficient approach for preparing 4,5-unsaturated alcohols. Synthetically useful functional groups,such as Cl, Br,carbonyl, and chloromethyl, remained intact during the functionalization reaction.The transition metal catalyzed functionalization of olefins is ap owerful tool to convert readily available petrochemical feedstocks into valuable synthetic building blocks. [1] The development of convenient and efficient methods for the functionalization of olefins is still ar esearch hotspot in organic synthesis although many catalytic methods for the mono-and di-functionalization of olefins have been reported over the past years.Many kind of metals,such as palladium, [2] rhodium, [3] gold, [4] nickel, [5] and copper, [6] were employed as the catalysts for this purpose.Direct carbohydroxylation of alkenes,w hich is the addition of C( alkyl and aryl) and OH to alkenes,i sa n important synthetic method for functionalization of the C=C bond. However,tothe best of our knowledge,only few papers on direct carbohydroxylation, namely arylhydroxylation of alkenes,h ave been reported, and they involve ar adical process. [7] Some examples of indirect carbohydroxylation of alkenes are known. [8] In addition, catalytic allylation of olefins,aH eck-type coupling reaction using allylic ethers, [9] allylic carbonates, [9] allylic tosylate, [10] and allylic alcohols [11] as allyl sources have also been reported. However,a sf ar as we know,t here is no precedent of direct addition of allylic alcohols to alkenes using transition-metal catalysts.H erein, we report that aw ide range of arylalkenes react with allylic alcohols under the cooperative catalysis of Cu, Ag, and[*] W. Ahmed, [+] Dr.

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Catalyst‐Controlled Highly Selective Coupling and Oxygenation of Olefins: A Direct Approach to Alcohols, Ketones, and Diketones

Cited by 188 publications

References 112 publications

Iron Catalysis in Organic Synthesis

Iron Catalysis in Organic Synthesis

Copper(ii)-catalyzed coupling reaction: an efficient and regioselective approach to N′,N′-diaryl acylhydrazines

Direct Carbohydroxylation of Arylalkenes with Allylic Alcohols: Cooperative Catalysis of Copper, Silver, and a Brønsted Acid

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