Preparation of allylboronates by Pd-catalysed borylative cyclisation of dienynes

López-Durán, Ruth; Martos-Redruejo, Alicia; Buñuel, Elena; Pardo‐Rodriguez, Virtudes; Cárdenas, Diego J.

doi:10.1039/c3cc45879b

Cited by 23 publications

(11 citation statements)

References 39 publications

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“…Polyunsaturated derivatives were also suitable substrates for Pd‐catalyzed borylative cyclization. Dienynes derived from 1,6‐enynes by formal addition of a second alkene conjugated to the existing one reacted under catalysis by Pd(TFA) 2 to give exocyclic allylboronates (Scheme ) . These products could have been expected according to the reaction outcome observed for simple 1,6‐enynes described above.…”

Section: Borylative Cyclization Involving the Formation Of C–c Bondsmentioning

confidence: 91%

Borylative Cyclization Reactions

Buñuel

Cárdenas

2016

Eur J Org Chem

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Borylative cyclizations constitute a family of important cascade reactions for the formation of carbo‐ and heterocycles containing boryl substituents. These compounds are formed from a variety of starting mono‐ and polyunsaturated substrates in metal‐catalyzed or boron‐mediated processes, and can be employed in subsequent functionalization. Here we review recently reported borylative cyclization reactions with special emphasis on metal‐catalyzed processes. These may involve the formation of one or several rings and the formation of a C–B bond in a domino process taking place within the same synthetic operation.

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Section: Borylative Cyclization Involving the Formation Of C–c Bondsmentioning

confidence: 91%

Borylative Cyclization Reactions

Buñuel

Cárdenas

2016

Eur J Org Chem

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“…[12d] Using the same catalyst, borylative cyclization of 1,3-dien-8-ynes was reported to give allylic boronates having five or six membered carboor heterocycles. [30] Later they also demonstrated that changing the ligand can control the reaction outcome. [11] An allylic carbonate containing enynes gave decarboxylative borylation products (allylboronates) when Pd(OAc) 2 was used as a catalyst and NHC as a ligand (IMes = 1,3-bis(2,4,6-trimethylphenyl)-imidazolium), whereas replacing the NHC with PCy 3 gave borylative cyclization products (alkenylboronates).…”

Section: Palladium-catalyzed Hydroboration Of Enynesmentioning

confidence: 99%

“…In 2012, Cárdenas and co‐workers reported Pd(TFA) 2 (TFA=trifluoroacetate) catalyzed borylative cyclization of 1,7‐enynes which led to formation of six‐membered rings via 1,8‐hydroboration followed by cyclization . Using the same catalyst, borylative cyclization of 1,3‐dien‐8‐ynes was reported to give allylic boronates having five or six membered carbo‐ or heterocycles . Later they also demonstrated that changing the ligand can control the reaction outcome .…”

Section: Catalytic Hydroboration Of Enynesmentioning

confidence: 99%

Hydroboration of Enynes and Mechanistic Insights

Mao

Bose

2020

Adv Synth Catal

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Organoboron compounds have found broad applications in the construction of novel CÀ C, CÀ O, and CÀ N bonds via transition metal-catalyzed reactions. The hydroboration of CÀ C multiple bonds is one of the most important methodologies to introduce the boron atom into the organic skeleton. Traditionally, boranes were employed in the hydroboration of enynes under transition metal-free conditions. When precious metal catalysts, such as palladium and rhodium were employed in the reactions, the scope of the hydroboration, as well as the regio-and stereoselectivity, was improved. The asymmetric hydroboration of enynes was also achieved via Pd-catalyzed reactions. In recent years, the non-precious 3d-metal catalysts, such as iron, cobalt, nickel and copper were employed in the hydroboration of enynes, especially in the enantiose-lective reactions. In this review, we have looked into the hydroboration of enynes as well as their mechanisms. Catalytic Hydroboration of Enynes 3.1. Precious Metal-Catalyzed Hydroboration of Enynes 3.2 Nonprecious Metal-Catalyzed Hydroboration of Enynes 4. Conclusion and Outlook

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“…Borylative cyclization of 1,6-enynes containing a second olefinic bond with bis(picolinato)diboron in the presence of a Pd catalyst and MeOH gives five-membered carbocycles (Scheme 28). 76 The reactions are suggested to proceed via η 3 -allyl complexes, leading to products with boron at the terminal position.…”

Section: Cyclization Of Dienynes and Enediynesmentioning

confidence: 99%

Silylboranes as Powerful Tools in Organic Synthesis: Stereo- and Regioselective Reactions with 1,n-Enynes

Moberg

2020

Synthesis

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Bismetalated alkenes, accessible by element–element addition to alkynes, are valuable building blocks in organic synthesis, providing wide opportunities for divergent synthesis. Silaboration of alkynes with a pendant olefinic group, catalyzed by group 10 metal complexes, and subsequent transformation of the silicon and boron functional groups give access to densely functionalized 1,3-dienes and 1,3,5-trienes with defined stereo- and regiochemistry, 1,2-dienes, and carbocyclic and heterocyclic products.1 Introduction2 Background3 Reactions with 1,3-Enynes4 Cyclization 1,6-Enynes5 Cyclization 1,7-Enynes6 Cyclization of 1,n-Enynes (n > 7)7 Cyclization of Dienynes and Enediynes8 Cyclization of 1,6-Diynes9 Conclusions

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Preparation of allylboronates by Pd-catalysed borylative cyclisation of dienynes

Cited by 23 publications

References 39 publications

Borylative Cyclization Reactions

Borylative Cyclization Reactions

Hydroboration of Enynes and Mechanistic Insights

Silylboranes as Powerful Tools in Organic Synthesis: Stereo- and Regioselective Reactions with 1,n-Enynes

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