Qiao-qiao Teng and Ming Chen of Changzhou University showed that barium oxide
is a strong enough base to doubly deuterate an alkyl nitrile 1, leading to
2
(Eur. J. 1196154-13-8 Chemscene Org. Chem. PMID:24516446 2022, e202201218.
DOI: 10.1002/ejoc.202201218).
Hong-Hai Zhang of Nanjing Tech. University reported a complementary deuteration using a Pd catalyst
(J. Org. Chem. 2022, 87, 16084.
DOI: 10.1021/acs.joc.2c01654).
Christian Wolf of Georgetown University showed that LiI converted an
alkyl fluoride 3 to the alkyl iodide 4
(Synthesis 2022, 54, 4320.
DOI: 10.1055/s-0041-1738383).
Takaaki Sato of Keio University assembled the
enamide 7 by coupling the alkyne
5 with the dioxazolone 6
(Org. Lett. 2022, 24, 8662.
DOI: 10.1021/acs.orglett.2c03497).
Fraser F. (Bromomethyl)cycloheptane Purity Fleming of Drexel University showed that the formamide
9, prepared from the alkenyl iodide
8, could readily be dehydrated to the isonitrile
(Org. Lett. 2022, 24, 8657.
DOI: 10.1021/acs.orglett.2c03461).
David E. Olson of the University of California, Davis used trimethylsilyl iodide
followed by base to convert the carbamate 10 to the tertiary
amine 11
(Org. Lett. 2022, 24, 6208.
DOI: 10.1021/acs.orglett.2c02516).
Takaaki Kamishima of the Genesis Research Institute used an Ir
catalyst under a hydrogen atmosphere to rearrange the allylic alcohol 12 to the
unsaturated aldehyde 13
(Eur. J. Org. Chem. 2022, e202201002.
DOI: 10.1002/ejoc.202201002).
Changkun Li of Shanghai Jiao Tong University prepared the enol ester 15 by
coupling the allene 14 with benzoic acid
(Org. Chem. Front. 2022, 9, 6869.
DOI: 10.1039/D2QO01153K).
Serge Ruccolo and Gilmar Brito of Merck Rahway reported using electrolysis to
regenerate ATP, driving the construction of the nucleoside 18 by the enzymatic
coupling of the ribose derivative 16 with uracil 17
(J. Am. Chem. Soc. 2022, 144, 22582.
DOI: 10.1021/jacs.2c08955).
Patrycja Żak of the Adam Mickiewicz University in Poznan used an
N-heterocyclic carbene to catalyze the combination of the unsaturated aldehyde
19 with the thiol 20, to give the
thioester 21
(Org. Chem. Front. 2022, 9, 4846.
DOI: 10.1039/D2QO00678B).
Fu-Min Zhang of Lanzhou University prepared the
thioamide 24 by combining
the nitrile 22 with the alkyl bromide 23
(Chem. Commun. 2022, 58, 11430.
DOI: 10.1039/D2CC04210J).
Keyume Ablajan of Xinjiang University showed that activation of the hydrazide 25 with
iodine gave an intermediate that coupled with aniline, leading to the
amide 26
(Synthesis 2022, 54, 4353.
DOI: 10.1055/a-1838-9491).
Jeffrey N. Johnston of Vanderbilt University fluorinated the nitroalkane
27, then combined that product with the N-hydroxy
amine 28 to give the amide 29
(J. Am. Chem. Soc. 2022, 144, 16708.
DOI: 10.1021/jacs.2c05986).
Luminamicin, an antiobiotic isolated from the culture broth of an actinomycete strain OMR-59,
contains an unusual cyclic enol ether. Tomoyasu Hirose and Toshiaki Sunazuka of Kitasato University
took advantage of this, preparing the enol ether 32 by coupling the alcohol 31 with
the α-chloro sulfide 30
(J. Am. Chem. Soc. 2022, 144, 23148.
DOI: 10.1021/jacs.2c10856).
