Functionalization of Csp3–H bond—Sc(OTf)3-catalyzed domino 1,5-hydride shift/cyclization/Friedel–Crafts acylation reaction of benzylidene Meldrum’s acids

Mahoney, Stuart J.; Moon, David T.; Hollinger, Jon; Fillion, Eric

doi:10.1016/j.tetlet.2009.06.007

Cited by 77 publications

(18 citation statements)

References 27 publications

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“…Scandium(III) triflate proved to be an excellent catalyst for the transformation of 122 to 123 through 1,5-hydride shift/ring closure. [60] This reaction proceeded readily at room temperature. When conducted at 100 8C, the reaction cascade was extended further to include a Friedel-Crafts acylation (122!124).…”

Section: Amines As Hydride Donorsmentioning

confidence: 96%

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CH Bond Functionalization through Intramolecular Hydride Transfer

2014

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Known for over a century, reactions that involve intramolecular hydride-transfer events have experienced a recent resurgence. Undoubtedly responsible for the increased interest in this research area is the realization that hydride shifts represent an attractive avenue for C-H bond functionalization. The redox-neutral nature of these complexity-enhancing transformations makes them ideal for sustainable reaction development. This Review summarizes recent progress in this field while highlighting key historical contributions.

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Section: Amines As Hydride Donorsmentioning

confidence: 96%

“…(16 a) and (16 b)]. Scandium(III) triflate proved to be an excellent catalyst for the transformation of 122 to 123 through 1,5‐hydride shift/ring closure 60. This reaction proceeded readily at room temperature.…”

Section: Ch Functionalization By Intramolecular Hydride Transfermentioning

confidence: 99%

CH Bond Functionalization through Intramolecular Hydride Transfer

2014

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“…In 2009, Fillion and co‐workers reported a convenient one‐pot construction of tetrahydrobenzo[ b ]fluoren‐11‐ones 192 under Sc(OTf) 3 catalysis (Scheme ) 54. Three new bonds: a CH and two CC bonds were formed in the cascade process.…”

Section: Benzylic C(sp3)h Bondsmentioning

confidence: 99%

Advancement in Cascade [1,n]‐Hydrogen Transfer/Cyclization: A Method for Direct Functionalization of Inactive C(sp³)H Bonds

2014

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The cascade [1,n]-hydrogen transfer/cyclization, recognized one century ago, has received considerable interest in recent decades and great achievements have been made. This cascade process can functionalize CA C H T U N G T R E N N U N G (sp 3 ) À H bonds directly into C À C, C À N, C À O bonds under the catalysis by Lewis acids, Brønsted acids or organocatalysts, and even under thermal conditions. This methodology has shown preeminent power to construct 5-or 6-membered heterocyclic as well as all-carbon rings. In this review, various hydrogen donors and hydrogen acceptors are categorized and discussed.

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“…In search for ways to overcome this apparent limitation, Sames (Scheme a, b) and Fillion (Scheme c) found that benzylic methylene groups can also function as hydride donors (Scheme ) 5. 27 However, an electron‐rich aromatic ring ( 44 , 46 and 48 ) was required to accelerate the hydride‐transfer process.…”

Section: Hydride Transfer and Cyclization Of Unactivated Ch Bondsmentioning

confidence: 99%

The Redox‐Neutral Approach to CH Functionalization

Peng

Maulide

2013

Chemistry A European J

289

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The direct functionalization of C-H bonds is an attractive strategy in organic synthesis. Although several advances have been made in this area, the selective activation of inert sp(3) C-H bonds remains a daunting challenge. Recently, a new type of sp(3) C-H activation mode through internal hydride transfer has demonstrated the potential to activate remote sp(3) C-H linkages in an atom-economic manner. This Minireview attempts to classify recent advances in this area including the transition to non-activated sp(3) C-H bonds and asymmetric hydride transfers.

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Functionalization of Csp3–H bond—Sc(OTf)3-catalyzed domino 1,5-hydride shift/cyclization/Friedel–Crafts acylation reaction of benzylidene Meldrum’s acids

Cited by 77 publications

References 27 publications

CH Bond Functionalization through Intramolecular Hydride Transfer

CH Bond Functionalization through Intramolecular Hydride Transfer

Advancement in Cascade [1,n]‐Hydrogen Transfer/Cyclization: A Method for Direct Functionalization of Inactive C(sp³)H Bonds

The Redox‐Neutral Approach to CH Functionalization

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Functionalization of Csp3–H bond—Sc(OTf)3-catalyzed domino 1,5-hydride shift/cyclization/Friedel–Crafts acylation reaction of benzylidene Meldrum’s acids

Cited by 77 publications

References 27 publications

CH Bond Functionalization through Intramolecular Hydride Transfer

CH Bond Functionalization through Intramolecular Hydride Transfer

Advancement in Cascade [1,n]‐Hydrogen Transfer/Cyclization: A Method for Direct Functionalization of Inactive C(sp3)H Bonds

The Redox‐Neutral Approach to CH Functionalization

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Advancement in Cascade [1,n]‐Hydrogen Transfer/Cyclization: A Method for Direct Functionalization of Inactive C(sp³)H Bonds