loudon 6th edition organic chemistry A tandem reaction is a reaction in which several bonds are formed in sequence withoutisolating intermediates. The tandem reaction below goes through three key reactions: a) aSuzuki-type coupling to generate 3, then b) deprotection of R₁ and installation of a triflateleaving group to generate 4, and finally c) a Heck-type coupling reaction to make 5. Usingyour knowledge of metal-catalyzed coupling reactions, please answer the followingquestions.OMePd(PPh3)4 (or PdL4)OR₁1) TBAF (TBS deprotection)34NaOEt, THF (solvent), 50 °C R₁ = TBS2) TfO2, Et3NR₁ = TfPdL₂ cat.Et3N, THF 60 °CBrOHOMe1 R₁ = TBS(alcohol protectinggroup)SiHOB.2a) Draw the product 3 of the Suzuki-type coupling that occurs between 1 and 2.b) In 3, the R₁ group is TBS, a common protecting group for alcohols. Usingtetrabutylammonium fluoride (TBAF), this TBS group can be removed to regenerate thealcohol. In a second step, a triflate leaving group (OTf) is installed at this position. Thesetwo steps produce 4 which is primed to participate in the final Heck reaction. Please draw4.

Suzuki coupling reactionTBS deprotectionTriflate formationIntramolecular Heck coupling reaction

A tandem reaction is a reaction in which several bonds are formed in sequence without isolating intermediates. The tandem reaction below goes through three key reactions: a) a Suzuki-type coupling to generate 3, then b) deprotection of R₁ and installation of a triflate leaving group to generate 4, and finally c) a Heck-type coupling reaction to make 5. Using your knowledge of metal-catalyzed coupling reactions, please answer the following questions. OMe Pd(PPh3)4 (or PdL4) LOR₁ 1) TBAF (TBS deprotection) PdL₂ cat. 3 4 NaOEt, THF (solvent), 50 °C R₁ = TBS 2) TfO2, Et3N R₁ = Tf Et3N, THF 60 °C Br OMe 1 R₁ = TBS (alcohol protecting group) OH B HO 2 a) Draw the product 3 of the Suzuki-type coupling that occurs between 1 and 2. b) In 3, the R₁ group is TBS, a common protecting group for alcohols. Using tetrabutylammonium fluoride (TBAF), this TBS group can be removed to regenerate the alcohol. In a second step, a triflate leaving group (OTf) is installed at this position. These two steps produce 4 which is primed to participate in the final Heck reaction. Please draw 4.

A tandem reaction is a reaction in which several bonds are formed in sequence without isolating intermediates. The tandem reaction below goes through three key reactions: a) a Suzuki-type coupling to generate 3, then b) deprotection of R₁ and installation of a triflate leaving group to generate 4, and finally c) a Heck-type coupling reaction to make 5. Using your knowledge of metal-catalyzed coupling reactions, please answer the following questions. OMe Pd(PPh3)4 (or PdL4) LOR₁ 1) TBAF (TBS deprotection) PdL₂ cat. 3 4 NaOEt, THF (solvent), 50 °C R₁ = TBS 2) TfO2, Et3N R₁ = Tf Et3N, THF 60 °C Br OMe 1 R₁ = TBS (alcohol protecting group) OH B HO 2 a) Draw the product 3 of the Suzuki-type coupling that occurs between 1 and 2. b) In 3, the R₁ group is TBS, a common protecting group for alcohols. Using tetrabutylammonium fluoride (TBAF), this TBS group can be removed to regenerate the alcohol. In a second step, a triflate leaving group (OTf) is installed at this position. These two steps produce 4 which is primed to participate in the final Heck reaction. Please draw 4.

Pushing Electrons

4th Edition

ISBN:9781133951889

Author:Weeks, Daniel P.

Publisher:Weeks, Daniel P.

Chapter1: Lewis Structures

Section: Chapter Questions

Problem 73EQ

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