2020
DOI: 10.1021/acs.orglett.0c00988
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Abstract: A new reduction of carbamates to N-methyl amines is presented. The magnesium-catalyzed reduction reaction allows the conversion of cyclic and linear carbamates, including N-Boc protected amines, into the corresponding N-methyl amines and amino alcohols which are of significant interest due to their presence in many biologically active molecules. Furthermore, the reduction can be extended to the formation of N-trideuteromethyl labeled amines.

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Cited by 26 publications
(26 citation statements)
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References 70 publications
(18 reference statements)
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“…As previously reported, hydroboration reactions using MgBu 2 as the catalyst occur via in situ formation of the active catalytic species BuMg–H. 11 The energy profile for the formation of BuMg–H by the reaction of MgBu 2 with HBpin is discussed in Figure S1 (see the Supporting Information). Within the reaction conditions used in this work, BuMg–H can be stabilized by solvent molecules (THF), by HBpin, or by 1i , as shown in Figure S2 .…”
Section: Mechanistic Studymentioning
confidence: 62%
See 1 more Smart Citation
“…As previously reported, hydroboration reactions using MgBu 2 as the catalyst occur via in situ formation of the active catalytic species BuMg–H. 11 The energy profile for the formation of BuMg–H by the reaction of MgBu 2 with HBpin is discussed in Figure S1 (see the Supporting Information). Within the reaction conditions used in this work, BuMg–H can be stabilized by solvent molecules (THF), by HBpin, or by 1i , as shown in Figure S2 .…”
Section: Mechanistic Studymentioning
confidence: 62%
“… 10 In certain cases, even low-cost and readily available dialkylmagnesium could be applied as a catalyst. 11 Given the current limitations in the catalytic regiodivergent ring opening of epoxides, we decided to explore whether simple magnesium catalysts would allow for the selective C–O bond activation, leading to either branched or linear alcohols in good yields and with broad functional group tolerance ( Scheme 1 b). We here report the development of such a regiodivergent reaction and explain the mechanism supported by experiment and computation.…”
Section: Introductionmentioning
confidence: 99%
“…The thermal ellipsoids are shown at 50 %p robability,a nd all the hydrogen atoms (except for H(1) from structure 2d and H(7), H(16), from structure 2ee)are deleted for clarity.Selected bond lengths []and angles (deg), For 2d (left): O1-C1 1.2115(13),N 1-C1 1.3718(13),N 1-B1 1.4446(13), N1-C2 1.4485(12);O1-C1-N1 124.97(10), C1-N1-B1 119.88(9), C1-N1-C2 117.43(8). For 2ee (right): O1-C7 1.2265(17), N1-C7 1.3443(18),N 1-C1 1.4100(17);O1-C7-N1 124.64(13), C7-N1-C1 125.84(12);O 2-C16 1.2327(17), N2-C16 1.3383(18), N2-C10 1.4144(17);O2-C16-N2 124.85(13),C 16-N2-C101 24.22(12) [33].…”
mentioning
confidence: 99%
“…3) first example for the selective C-N bond cleavage by transfer hydrogenation of amides 2) first example for the transfer hydrogenation of carbamates 1) first example for the transfer hydrogenation of urea derivatives Mn c. This work Please do not adjust margins Please do not adjust margins Numerous procedures have been developed for the reduction of amide-related substrates, e.g. hydrogenation 40 , hydrosilylation [41][42][43] and hydroborylation 44,45 . Among them, hydrogenation methods stand out as a green approach.…”
Section: Introductionmentioning
confidence: 99%