2021
DOI: 10.1021/acs.orglett.1c01224
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Rh(II)-Catalyzed C–H Alkylation of Benzylamines with Unactivated Alkenes: The Influence of Acid on Linear and Branch Selectivity

Abstract: The Rh-catalyzed C−H alkylation of benzylamine derivatives with unactivated 1-alkenes that proceeds via a picolinamide directing group is reported. The crucial role of an acid additive in this transformation is confirmed. Aromatic acids showed high linear selectivity, and aliphatic acids provided branched alkylation products as the major product. The reaction has a broad scope for benzylamines and alkenes. Deuterium labeling experiments suggest that a Rh-carbene intermediate is involved in the case of linear p… Show more

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Cited by 10 publications
(3 citation statements)
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“…In 2021, Das and Chatani studied the influence of acid additives on linear and branched selective alkylation reactions (Scheme 21). 75 They reported picolinamide directed Rh( ii )-catalyzed C–H bond alkylation of benzylamine 21a derivatives with unreactive alkenes 21b . In the presence of aromatic acid, high linear selectivity was obtained for 21c .…”
Section: Alkylation Via C–h Bond Activationmentioning
confidence: 99%
“…In 2021, Das and Chatani studied the influence of acid additives on linear and branched selective alkylation reactions (Scheme 21). 75 They reported picolinamide directed Rh( ii )-catalyzed C–H bond alkylation of benzylamine 21a derivatives with unreactive alkenes 21b . In the presence of aromatic acid, high linear selectivity was obtained for 21c .…”
Section: Alkylation Via C–h Bond Activationmentioning
confidence: 99%
“…Since the first example of the ortho -C–H alkylation of aromatic ketones with alkenes using Ru catalysis, a large number of reports on directed C–H alkylation with alkenes have appeared. However, most of these reactions were based on a linear-selective transformation, and only a limited number of studies have dealt with a branch-selective transformation. , In addition, the reported branch-selective alkylation reactions mostly involved the use of activated alkenes such as styrenes, acrylate esters, and vinyl esters. Our group recently reported the first example of the branch-selective alkylation of sulfonamides with vinylsilanes (Scheme B) .…”
Section: Introductionmentioning
confidence: 99%
“…Rovis and co-workers demonstrated the intramolecular version for hydroarylation of highly substituted olefins under Rh­(III) catalysis . Alternatively, the hydroarylation reaction of 1,1-disubstituted olefin has been explored by structural and/or electronic modification of olefins . For example, 1,1-disubstituted methylene cyclic compounds with cyclopropane, cyclobutane, aziridine, and carbonate groups have been applied.…”
mentioning
confidence: 99%