Palladium-catalyzed reaction of allylic ammonium bromides with nucleophiles

Hirao, Toshikazu; Yamada, Naoto; Ohshiro, Yoshiki; Agawa, Toshio

doi:10.1016/s0022-328x(00)86917-x

Cited by 49 publications

(14 citation statements)

References 11 publications

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“…A quaternary ammonium salt is one of the most common N-containing substrates in organic synthesis. 247 2 , which undergoes a reductive elimination to yield the final product. Analogously, aryltrimethylammonium salts could be applied to Suzuki cross-coupling, 254 Negishi cross-coupling, 255,256 and Buchwald−Hartwig amination 257 (Scheme 99).…”

Section: Quaternary Ammonium Saltsmentioning

confidence: 99%

Transition-Metal-Catalyzed Cleavage of C–N Single Bonds

et al. 2015

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Section: Quaternary Ammonium Saltsmentioning

confidence: 99%

Transition-Metal-Catalyzed Cleavage of C–N Single Bonds

et al. 2015

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“…82 Allylic products were obtained as a mixture of regioisomers. 82 Allylic products were obtained as a mixture of regioisomers.…”

Section: Palladium-catalyzed Allylic Substitutions With Allylic Aminesmentioning

confidence: 99%

Transition metal-catalyzed allylic substitution reactions with unactivated allylic substrates

2015

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The transition metal-catalyzed allylic substitution of unactivated allylic substrates (allylic alcohols, allylic ethers and allylic amines) is rapidly becoming an important area of research. There are several advantages to using these substrates in allylic substitution reactions: the use of unactivated alcohols minimizes the production of waste by-products and reaction steps; and allylic ethers and allylic amines are useful substrates because of their stability and their presence in numerous biologically active compounds. Research in this field has therefore gained widespread attention for promoting the development of efficient and environmentally benign procedures for the formation of C-C, C-N and C-O bonds.

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“…After g, 220 mmol), paraformaldehyde (7.27 g, 31 For allylic ammoniums as precursors of putative π-allyl Pd complexes, see for example refs. [125][126][127]. For sterically less demanding leaving groups, we also similarly prepared the known characterized precursor 29d, [128 -130] as well as the unreported analogs 29e and 29f.…”

Section: Methodsmentioning

confidence: 99%

A Concise Synthesis ofrac‐Ambrox®viathe Palladium(0)‐Catalyzed Carboalkoxylation of an Allylic Ammonium Salt, as Compared to a Formaldehyde HeteroDiels–AlderApproach

Chapuis

Skuy

Richard

2019

Helvetica Chimica Acta

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Acidic cyclization of either the diethylallylamines 29b or 30, followed by a 1.5 mol‐% Pd‐catalyzed carbomethoxylation of quaternized 31b, leads to the methyl ester 36a. This latter could also be obtained in optically pure form by carbomethoxylation of the corresponding (+)‐acetate. Final reduction‐cyclization may be conducted as earlier described, towards the desired odoriferous rac‐Ambrox® 38a, or its pure (−)‐enantiomer. Generation of a π‐allyl Pd complex from an allylic ammonium salt, followed by carboalkoxylation is novel. In only five chemical steps starting from farnesene 2, the present work constitutes the most concise total synthesis of rac‐Ambrox® 38a to date.

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Palladium-catalyzed reaction of allylic ammonium bromides with nucleophiles

Cited by 49 publications

References 11 publications

Transition-Metal-Catalyzed Cleavage of C–N Single Bonds

Transition-Metal-Catalyzed Cleavage of C–N Single Bonds

Transition metal-catalyzed allylic substitution reactions with unactivated allylic substrates

A Concise Synthesis ofrac‐Ambrox®viathe Palladium(0)‐Catalyzed Carboalkoxylation of an Allylic Ammonium Salt, as Compared to a Formaldehyde HeteroDiels–AlderApproach

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