Efficient access to unprotected primary amines by iron-catalyzed aminochlorination of alkenes

Article abstract of DOI:10.1126/science.aat3863

Primary amines are essential constituents of biologically active molecules and versatile intermediates in the synthesis of drugs and agrochemicals. However, their preparation from easily accessible alkenes remains challenging. Here, we report a general strategy to access primary amines from alkenes through an operationally simple iron-catalyzed aminochlorination reaction. A stable hydroxylamine derivative and benign sodium chloride act as the respective nitrogen and chlorine sources. The reaction proceeds at room temperature under air; tolerates a large scope of aliphatic and conjugated alkenes, including densely functionalized substrates; and provides excellent anti-Markovnikov regioselectivity with respect to the amino group. The reactivity of the 2-chloroalkylamine products, an understudied class of amphoteric molecules, enables facile access to linear or branched aliphatic amines, aziridines, aminonitriles, azido amines, and homoallylic amines.

Full text of DOI:10.1126/science.aat3863

RESEARCH
tivate the olefin with an aryl substituent, or gen-
erate hazardous azide intermediates (Fig. 1A).
Falck and Kürti recently reported the prepara-
tion of a wide range of NH-aziridines via rhodium
catalysis, a reaction that addresses some impor-
tant challenges in this area (22, 23). However,
the application of this reaction is limited by the
challenges associated with the subsequent regio-
selective opening of the aziridines to reveal the
desirable primary amine building blocks, as well
as the high cost of rhodium. Thus, the direct cat-
alytic and regioselective synthesis of unprotected
amine derivatives from unactivated alkenes re-
mains an unsolved challenge in organic chemistry.
A catalytic method to introduce both the de-
sired unprotected amine group, ideally at the
more challenging primary position, and a ver-
satile electrophile at the secondary position
would prove particularly useful in the prepara-
tion of important compounds because of the
complementary reactivity of these functional
groups. Ideally, these products could be accessed
by using a simple protocol, inexpensive reagents,
and an Earth-abundant metal catalyst. Unpro-
tected 2-chloroalkylamines would, in principle,
fulfill the role of amphoteric aminated build-
ing blocks. These seemingly unstable molecules
have rarely been reported in the literature (24), and
the few viable synthetic methods to access them
have generally relied on the direct chlorination
of amino alcohols (25) or the ring opening of NH-
aziridines (26). Alternatively, derivatives protected
by a tosyl (Ts) group can be occasionally accessed
ORGANIC CHEMISTRY
Efficient access to unprotected
primary amines by iron-catalyzed
aminochlorination of alkenes
Luca Legnani1*, Gabriele Prina-Cerai1*, Tristan Delcaillau1,2†,
Suzanne Willems1†, Bill Morandi1,2
‡
Primary amines are essential constituents of biologically active molecules and
versatile intermediates in the synthesis of drugs and agrochemicals. However, their
preparation from easily accessible alkenes remains challenging. Here, we report a
general strategy to access primary amines from alkenes through an operationally
simple iron-catalyzed aminochlorination reaction. A stable hydroxylamine derivative
and benign sodium chloride act as the respective nitrogen and chlorine sources. The
reaction proceeds at room temperature under air; tolerates a large scope of aliphatic
and conjugated alkenes, including densely functionalized substrates; and provides
excellent anti-Markovnikov regioselectivity with respect to the amino group. The reactivity
of the 2-chloroalkylamine products, an understudied class of amphoteric molecules,
enables facile access to linear or branched aliphatic amines, aziridines, aminonitriles, azido
amines, and homoallylic amines.
liphatic primary amines are present in a
wide range of important bioactive com-
pounds. They are also among the most
versatile synthetic intermediates in the
atom-economical construction of second-
starting material. A complementary and poten-
tially more versatile alternative would use ubiqui-
tous alkenes, which are commonly encountered
in petrochemical feedstocks and synthetic in-
termediates, as starting materials (7). Although
aminofunctionalization reactions, such as hy-
droamination (8–13) and aminohydroxylation
(14–17) of alkenes and alkene azidation (18–21),
have played an important role in this area, these
reactions are generally limited by the need to
protect (and later deprotect) the nitrogen, ac-
A
ary amines, tertiary amines, and heterocycles
(1). The synthesis of primary amines traditionally
relies on reductive amination (2, 3), dehydroge-
native coupling of alcohols (4), allylic amination
(5, 6), or azide or nitrile reduction. These methods
rely on the preinstallation of a polar group in the
1Max-Planck-Institut für Kohlenforschung, Mülheim an der
Ruhr, Germany. 2ETH Zürich, Zürich, Switzerland.
*These authors contributed equally to this work.
†These authors contributed equally to this work.
‡Corresponding author. Email: morandib@ethz.ch
Fig. 1. Development of a strategy for the synthesis of a broad class of unprotected amines. (A) Traditional approach for primary amine synthesis.
X, polar group or H; PG, protecting group. (B) Our design for direct radical trapping. R, any group; Ph, phenyl; SET, single electron transfer. (C) Reaction
development (selected conditions). Piv, pivaloyl; Tf, trifluoromethanesulfonyl; TMSCl, trimethylsilyl chloride; phth, phthalimide.
Legnani et al., Science 362, 434–439 (2018)
26 October 2018
1 of 5

RESEARCH
| REPORT
from alkenes by using stoichiometric protocols,
but these reactions are limited by the challenging
selective cleavage of the Ts group in the presence
of the chloride and the lack of regioselectivity,
as well as poor scope and yield (27–32). An intra-
molecular iron-catalyzed aminochlorination has
been reported by Bach et al., though the products
are chlorosubstituted oxazolidinones rather than
unprotected 2-chloroalkylamines (33–35).
In iron-catalyzed amination reactions of alkenes
more generally (11, 15–17, 36–41), the use of spe-
cific substituents (e.g., Ts) on the nitrogen atom
to control reactivity and the high inefficiency
when using unactivated olefins remain limiting
factors. To collectively address these issues, we
reasoned that the use of chloride as a nucleophile
in electrophilic amination reactions would not
only enable access to versatile 2-chloroalkylamines
but also provide a strategy to address the lack of
reactivity observed with traditionally unreactive
alkenes. Related (15, 16) iron-catalyzed amino-
hydroxylation reactions and etherifications have
a limited substrate scope because they rely on
a mechanism that involves a single electron
transfer–mediated oxidation of a carbon-centered
radical to a carbocation, a process that becomes
very challenging when nonbenzylic radicals are
generated as intermediates (Fig. 1B, Eq. 3). On
the basis of Bach’s precedent (Fig. 1B, Eq. 1) and
the well-known propensity of the chlorine atom
to undergo homolytic substitution reactions (42),
we hypothesized that the putative unstable rad-
ical intermediate generated through the attack
of a nitrogen-centered radical on a C=C double
bond could instead rapidly undergo chlorine
atom transfer from the amine-bound iron(III)
complex to form the desired product and regen-
erate the iron(II) catalyst (Fig. 1B, Eq. 2). In this
strategy, the facile homolytic substitution reac-
tion of the carbon radical with the iron-bound
chlorine atom, a pathway not easily accessible
with oxygen-containing ligands, provides a direct
route to product formation that does not involve
any additional single electron transfer step or
cationic intermediates. Consequently, a broader
palette of alkenes should be amenable to this new
process.
Herein, we report the iron-catalyzed amino-
chlorination of a wide range of conjugated and
nonconjugated alkenes, including densely func-
tionalized substrates. The reaction proceeds with
excellent regioselectivity for the linear amine [the
minor branched isomer could not be detected by
proton nuclear magnetic resonance (H-NMR)
spectroscopy] and leads to the direct formation
of unprotected 2-chloroalkylamines under oper-
ationally simple conditions.
Initial proof-of-concept experiments were con-
ducted under air with a stoichiometric amount
of FeCl2 added to a solution of 1-dodecene (a
traditionally challenging substrate in electro-
philic amination reactions) in the presence of a
variety of hydroxylamine-derived reagents (Fig. 1C
and table S1). A substantial conversion to the
product was observed, albeit in low yields be-
cause of the product’s instability in the presence
of excess Lewis acidic iron salts. We then ex-
plored different chloride sources to move away
from the use of stoichiometric amounts of iron
salts. Although trimethylsilyl chloride, the source
used by Bach et al. (33–35), gave moderate yields
of product, we discovered that the much more
benign and easy-to-handle sodium chloride gave
superior results. We believe that the use of a mild,
non–Lewis acidic source of chloride is crucial to
prevent the undesired decomposition of the rela-
tively unstable aminochlorinated product. Opti-
mal conditions for the reaction used inexpensive
iron(II) acetylacetonate [Fe(acac)2] as a catalyst,
simple sodium chloride as a chloride source, and
a hydroxylamine-derived reagent as an amine
source at room temperature in a methanol-
dichloromethane mixture. The 2-chloroalkylamine
was isolated in 72% yield with no detected al-
ternative regioisomers. The aminating reagent
Fig. 2. Scope of the reaction with activated and unactivated alkenes. All yields, unless
otherwise noted, are isolated yields of the 2-chloroalkylamine products. *Yields refer to
the isolated aziridine products after basic workup. †Diastereomeric ratio of the isolated
aziridine products. ‡(E )-Alkene isomer used as substrate. §(Z)-alkene isomer used as substrate.
||1H-NMR yield; see the supplementary materials for isolation and characterization.
dr, diastereomeric ratio; r.t., room temperature.
Legnani et al., Science 362, 434–439 (2018)
26 October 2018
2 of 5

RESEARCH
| REPORT
Fig. 3. Synthetic utility of 2-
chlorododecan-1-amine. All yields,
unless otherwise noted, are isolated
yields of the products. Reaction
conditions for the derivatizations of
2-chloro-1-amine are specified below
the products. tBu, tert-butyl; Et, ethyl;
aq., aqueous; TMS, trimethylsilyl;
DMF, dimethylformamide.
is thermally stable up to a temperature of 160°C,
as demonstrated by differential scanning calorim-
etry (DSC) analysis (fig. S2).
disubstituted alkenes and even a trisubstituted
alkene (26) also gave the products in high yields
with partial retention of stereochemistry. Styrenes
(27 to 33) could also be used in this transforma-
tion; however, in this case, the instability of the
benzylic chlorides prevented the isolation of the
products. Instead, the corresponding aziridine
was isolated directly after basic workup. With
regard to the substrates that failed to produce
synthetically useful yields of products (fig. S3),
solubility issues encountered with cholesterol
derivatives and the lack of chemoselectivity with
polyolefin substrates account for most of the
limitations observed thus far.
We next probed the range of densely func-
tionalized substrates amenable to the reaction. A
derivative of isosorbide (34), a renewable feed-
stock, as well as several structurally complex terpene
derivatives (36, 37, 40, and 41) were amino-
chlorinated in good yields. More importantly,
nitrogen-based bioactive scaffolds, such as quin-
coridine (35), prolinol (39), and even unpro-
tected adenine (38), delivered the corresponding
aminated products. Such substrates would ar-
guably pose a great challenge to the vast majority
of other transition metal–catalyzed amination
reactions.
synthetic utility (Fig. 3). In particular, it was our
goal to address current challenges in amination
chemistry through the use of these amphoteric
building blocks. The catalytic synthesis of pri-
mary amines from terminal olefins has been
recognized as one of the top 10 challenges in
catalysis (43). 2-Chloroalkylamines can easily be
reduced to the corresponding amines (42), af-
fording a practical solution to this challenge.
Changing the reducing agent and solvent even
enables access to the Markovnikov hydroamina-
tion product (43), a process that probably pro-
ceeds through in situ generation of an aziridine
intermediate followed by reductive ring open-
ing. Common nucleophiles, such as azide (46)
and cyanide (47), led to a practical synthesis of
the corresponding products, which are versatile
building blocks for diamine and amino acid
synthesis, respectively. The corresponding azir-
idines (45) can also be easily accessed upon
simple treatment with a base, providing a con-
venient iron-based alternative to the rhodium
method reported by Kürti and Falck. Surpris-
ing reactivity was observed with allyl magnesium
bromide, as C–C bond formation occurred at
the a position relative to the amino group, lead-
ing to useful unprotected homoallylic amines
(44). This reaction likely proceeds through initial
HCl elimination to form an imine intermediate
that can subsequently be attacked by the Grignard
reagent.
We next explored the alkene substrate scope
of this reaction, including two gram-scale demon-
strations. A wide range of terminal alkenes, some
containing unprotected polar groups that are
traditionally problematic in transition metal
catalysis (e.g., cyano substrate 6 and hydroxy
substrates 3, 15, and 16), gave the correspond-
ing products in good yields (Fig. 2). Basic ter-
tiary nitrogen centers (35, 18, 38, and 39) were
also tolerated, an important prerequisite for the
application of any methodology for the discov-
ery of bioactive compounds. Heterocycles com-
monly used in drug discovery, such as tetrazole
(19), oxetane (20), and purine (38), could be
readily used, as could an alkyne (15). Further-
more, aromatic halides (12 and 13), which can
serve as handles for further functionalization
through cross-coupling, gave the desired product
in good yields. A striking feature of the reaction
was the exclusive formation of the monofunc-
tionalized product even in cases where two
alkenes were present in the starting material
(16, 17, and 34); the absence of difunctional-
ization product in the crude reaction mixture
suggests that the low solubility of the protonated
amine product prevents overfunctionalization.
The reaction is not limited to monosubstituted
alkenes. Both 1,1 (36 and 37)- and 1,2 (23 to 25)-
Unprotected 2-chloroalkylamines are rare com-
pounds whose reactivity has not yet been studied
extensively. Having a convenient method to access
them, we sought to explore their reactivity and
Legnani et al., Science 362, 434–439 (2018)
26 October 2018
3 of 5

RESEARCH
| REPORT
Fig. 4. Preliminary mechanistic experiments. (A) Conservation of stereoinformation with cyclodecene substrates indicating a syn addition mech-
anism. (B) Loss of stereoinformation with b-Me styrene compounds showing a stepwise mechanism with this class of substrates. (C) Radical
experiments supporting the intermediacy of a short-lived radical intermediate. (D) Preliminary Hammett study supporting a mechanism involving
an electrophilic amination mechanism. sx, Hammett constant; KX/KH, ratio of the two rates. (E) Lack of backbone rearrangement supporting
the absence of carbocationic intermediates.
Preliminary studies were performed to sup-
port our initial mechanistic hypothesis (Fig.
1B). The use of cis- and trans-cyclodecene led
to the isolation of the corresponding products
(49 and 25) in good yields and with good over-
all conservation of stereochemistry (Fig. 4A).
This result suggests an efficient formal syn deliv-
ery of the NH2 and Cl groups. A similar experi-
ment using both cis– and trans–b-methyl (b-Me)
styrene resulted in a completely different outcome
(Fig. 4B). The stereoinformation was entirely
lost in this case, and both starting materials led
to the same stereoisomer of the major product
after conversion to the aziridines through stereo-
invertive ring closing (44). This divergent out-
come between the two classes of substrates is
consistent with the proposed model (Fig. 1B),
wherein an amine-coordinated iron complex
rapidly delivers the chloride from the same face
with nonstabilized aliphatic alkenes as sub-
strates, whereas rapid oxidation of the radical
intermediate to a stable benzylic cation occurs
in styrenes, concomitant with stereochemical
randomization.
We next aimed to support experimentally
the postulated formation of the radical in the
aliphatic alkene reaction. Experiments using one
of the fastest radical clocks to detect the inter-
mediacy of short-lived radical species supported
the formation of radical intermediates, because
ring opening of the cyclopropane could be clearly
observed (Fig. 4C, Eq. 1). This result, combined
with the high stereoretention of the reaction with
aliphatic alkenes (Fig. 4A) and the lack of cy-
clization of another radical clock (Fig. 4C, Eq. 2),
supports the formation of a short-lived carbon-
centered radical intermediate. This conclusion was
further supported by radical trapping experiments
using TEMPO [(2,2,6,6-tetramethylpiperidin-1-yl)oxyl]
and BHT (3,5-di-tert-4-butylhydroxytoluene), which
did not substantially influence the reactivity
(Fig. 4C, Eq. 3). On the basis of those experiments,
we believe that the rate constant of the intra-
molecular chlorine atom transfer is very high,
although it cannot exceed the known rate con-
stant of the cyclopropyl radical clock (3 × 1011 s−1)
(45). A preliminary Hammett study showed a
rate increase for electron-rich substrates, a result
consistent with a mechanism involving the at-
tack of highly electrophilic aminating species
onto the alkene (Fig. 4D). Finally, we performed
a simple experiment aiming to trap a possible
carbocationic intermediate (Fig. 4E) through a
rapid cationic rearrangement. In contrast to pre-
vious reports (15, 46), no rearrangement was
observed under our reaction conditions, sup-
porting the operation of a distinct mechanistic
pathway.
Collectively, these results are best explained
by our initially proposed model and support
the direct intramolecular trapping of a short-lived
carbon-centered radical through intramolecular
syn-chlorine atom transfer from an amine-
coordinated iron(III)-Cl complex.
REFERENCES AND NOTES
1. L. Legnani, B. N. Bhawal, B. Morandi, Synthesis 49, 776–789
(2017).
2. T. Gross, A. M. Seayad, M. Ahmad, M. Beller, Org. Lett. 4,
2055–2058 (2002).
3. R. V. Jagadeesh et al., Science 358, 326–332 (2017).
4. C. Gunanathan, D. Milstein, Angew. Chem. Int. Ed. Engl. 47,
8661–8664 (2008).
Legnani et al., Science 362, 434–439 (2018)
26 October 2018
4 of 5

RESEARCH
| REPORT
5. C. Defieber, M. A. Ariger, P. Moriel, E. M. Carreira, Angew.
Chem. Int. Ed. Engl. 46, 3139–3143 (2007).
6. M. J. Pouy, L. M. Stanley, J. F. Hartwig, J. Am. Chem. Soc. 131,
11312–11313 (2009).
7. P. Dauban, B. Darses, A. Jarvis, in Comprehensive Organic
Synthesis, P. Knochel, G. A. Molander, Eds.
(Elsevier, ed. 2, 2014), chap. 7.19, pp. 538−604.
8. M. Beller, J. Seayad, A. Tillack, H. Jiao, Angew. Chem. Int.
Ed. Engl. 43, 3368–3398 (2004).
9. Y. Miki, K. Hirano, T. Satoh, M. Miura, Angew. Chem. Int.
Ed. Engl. 52, 10830–10834 (2013).
10. S. Zhu, N. Niljianskul, S. L. Buchwald, J. Am. Chem. Soc. 135,
15746–15749 (2013).
11. J. Gui et al., Science 348, 886–891 (2015).
12. D. G. Kohler, S. N. Gockel, J. L. Kennemur, P. J. Waller,
K. L. Hull, Nat. Chem. 10, 333–340 (2018).
13. A. J. Musacchio et al., Science 355, 727–730 (2017).
14. M. A. Andersson, R. Epple, V. V. Fokin, K. B. Sharpless,
Angew. Chem. Int. Ed. Engl. 41, 472–475 (2002).
15. L. Legnani, B. Morandi, Angew. Chem. Int. Ed. Engl. 55,
2248–2251 (2016).
24. P. Kovacic, M. K. Lowery, K. W. Field, Chem. Rev. 70, 639–665
(1970).
25. G. Berger et al., Tetrahedron Lett. 54, 545–548 (2013).
26. E. Leemans, S. Mangelinckx, N. De Kimpe, Synlett 2009,
1265–1268 (2009).
27. S. R. Chemler, M. T. Bovino, ACS Catal. 3, 1076–1091 (2013).
28. Y. Cai et al., J. Am. Chem. Soc. 133, 5636–5639 (2011).
29. M. T. Bovino, S. R. Chemler, Angew. Chem. Int. Ed. Engl. 51,
3923–3927 (2012).
30. Y. Cai et al., Chem. Commun.) 2013, 8054–8056 (2013).
31. F. Minisci, R. Galli, M. Cecere, Tetrahedron Lett. 7, 3163–3166
(1966).
32. F. Minisci, R. Galli, Tetrahedron Lett. 6, 1679–1684 (1965).
33. T. Bach, B. Schlummer, K. Harms, Chem. Commun. 2000,
287–288 (2000).
34. T. Bach, B. Schlummer, K. Harms, Chemistry 7, 2581–2594 (2001).
35. H. Danielec, J. Klügge, B. Schlummer, T. Bach, Synthesis 3,
551–556 (2006).
36. A. Correa, O. García Mancheño, C. Bolm, Chem. Soc. Rev. 37,
1108–1117 (2008).
37. D.-F. Lu, C.-L. Zhu, J. D. Sears, H. Xu, J. Am. Chem. Soc. 138,
46. R. R. Naredla, D. A. Klumpp, Chem. Rev. 113, 6905–6948 (2013).
ACKNOWLEDGMENTS
We thank B. Bhawal for critical proofreading of this manuscript and
our apprentice, S. Begoihn, for the synthesis of some compounds.
We also thank A. Pommerin for the DSC measurements. We
kindly thank B. List for sharing analytical equipment, and the MS
department of the MPI for technical assistance. Funding: Generous
funding from the Max Planck Society, the Max-Planck-Institut
für Kohlenforschung, the European Research Commission (grant
agreement ShuttleCat 757608), the ETH Zürich, and the Fonds der
Chemischen Industrie is acknowledged. Author contributions:
B.M., L.L., and G.P.-C. designed the project. L.L., G.P.-C., T.D.,
and S.W. performed the experiments and collected the data. All
authors analyzed the data and contributed to the writing of the
manuscript. L.L. and G.P.-C. contributed equally as first authors.
T.D. and S.W. contributed equally as third authors. Competing
interests: We declare no competing financial interests. Data and
materials availability: All experimental data are available in the
supplementary materials. X-ray structural data can be accessed
free of charge from the Cambridge Crystallographic Data Centre
under reference numbers CCDC-1863481 to CCDC-1863483.
16. D.-F. Lu, C.-L. Zhu, Z.-X. Jia, H. Xu, J. Am. Chem. Soc. 136,
13186–13189 (2014).
17. K. S. Williamson, T. P. Yoon, J. Am. Chem. Soc. 134,
12370–12373 (2012).
18. Y.-A. Yuan, D.-F. Lu, Y.-R. Chen, H. Xu, Angew. Chem. Int.
Ed. Engl. 55, 534–538 (2016).
11360–11367 (2016).
38. C.-L. Zhu, J.-S. Tian, Z.-Y. Gu, G.-W. Xing, H. Xu, Chem. Sci. 6,
3044–3050 (2015).
39. J.-S. Tian, C.-L. Zhu, Y.-R. Chen, H. Xu, Synthesis 47,
1709–1715 (2015).
40. E. R. King, E. T. Hennessy, T. A. Betley, J. Am. Chem. Soc. 133,
4917–4923 (2011).
41. E. T. Hennessy, R. Y. Liu, D. A. Iovan, R. A. Duncan, T. A. Betley,
SUPPLEMENTARY MATERIALS
www.sciencemag.org/content/362/6413/434/suppl/DC1
Materials and Methods
Supplementary Text
Figs. S1 to S6
Tables S1 to S4
19. N. Fu, G. S. Sauer, A. Saha, A. Loo, S. Lin, Science 357,
575–579 (2017).
20. K. Shen, Q. Wang, J. Am. Chem. Soc. 139, 13110–13116 (2017).
21. X. Geng, F. Lin, X. Wang, N. Jiao, Org. Lett. 19, 4738–4741
(2017).
22. J. L. Jat et al., Science 343, 61–65 (2014).
23. Z. Ma, Z. Zhou, L. Kürti, Angew. Chem. Int. Ed. Engl. 56,
9886–9890 (2017).
Chem. Sci. 5, 1526–1532 (2014).
References (47–56)
42. C. H. Schiesser, L. M. Wild, Tetrahedron 52, 13265–13314 (1996).
43. J. Haggin, Chem. Eng. News 71, 23–27 (1993).
44. A. Cruz, I. I. Padilla-Martínez, E. V. García-Báez, Tetrahedron
Asymmetry 21, 909–913 (2010).
21 February 2018; resubmitted 6 July 2018
Accepted 4 September 2018
10.1126/science.aat3863
45. D. C. Nonhebel, Chem. Soc. Rev. 22, 347–359 (1993).
Legnani et al., Science 362, 434–439 (2018)
26 October 2018
5 of 5

Efficient access to unprotected primary amines by iron-catalyzed aminochlorination of
alkenes
Luca Legnani, Gabriele Prina-Cerai, Tristan Delcaillau, Suzanne Willems and Bill Morandi
Science 362 (6413), 434-439.
DOI: 10.1126/science.aat3863
Salt and iron ease the way to amines
Adding nitrogen to carbon compounds is often a laborious process. The nitrogen typically needs protection to
prevent undesired reactivity, and the protecting groups can be hard to remove afterward. Legnani et al. report a versatile
method to add unadorned NH 2 from a hydroxylamine derivative directly to a double-bonded carbon center. A simple iron
catalyst manipulates chloride from table salt onto the adjacent carbon through a radical mechanism, where it is poised for
a wide variety of further functionalization options.
Science, this issue p. 434
ARTICLE TOOLS
http://science.sciencemag.org/content/362/6413/434
SUPPLEMENTARY
MATERIALS
http://science.sciencemag.org/content/suppl/2018/10/24/362.6413.434.DC1
REFERENCES
This article cites 55 articles, 5 of which you can access for free
http://science.sciencemag.org/content/362/6413/434#BIBL
PERMISSIONS
http://www.sciencemag.org/help/reprints-and-permissions
Use of this article is subject to the Terms of Service
Science (print ISSN 0036-8075; online ISSN 1095-9203) is published by the American Association for the Advancement of
Science, 1200 New York Avenue NW, Washington, DC 20005. 2017 © The Authors, some rights reserved; exclusive
licensee American Association for the Advancement of Science. No claim to original U.S. Government Works. The title
Science is a registered trademark of AAAS.