Zirconium-Catalyzed Intermolecular Double Hydrophosphination of Alkynes with a Primary Phosphine

Article abstract of DOI:10.1021/acscatal.6b01850

Catalytic double hydrophosphination of internal alkynes and primary phosphines is possible using a zirconium complex, [κ⁵-N,N,N,N,C-(Me₃SiNCH₂CH₂)₂NCH₂CH₂NSiMe₂CH]Zr (1). The reaction proceeds via stepwise hydrophosphination to give vinyl phosphine products, which can be isolated or further converted to the respective 1,2-bis(phosphino)ethane (i.e., double hydrophosphination). The catalysis is highly selective for formation of secondary phosphine products.

Full text of DOI:10.1021/acscatal.6b01850

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Letter
Zirconium-catalyzed intermolecular double
hydrophosphination of alkynes with a primary phosphine
Christine A Bange, and Rory Waterman
ACS Catal., Just Accepted Manuscript • DOI: 10.1021/acscatal.6b01850 • Publication Date (Web): 25 Aug 2016
Downloaded from http://pubs.acs.org on August 25, 2016
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ACS Catalysis
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Zirconium-Catalyzed Intermolecular Double Hydrophosphination of
Alkynes with a Primary Phosphine
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Christine A. Bange and Rory Waterman*
Department of Chemistry, University of Vermont, Burlington, Vermont 05405, United States
Supporting Information Placeholder
products, which can be prepared selectively using range of
ABSTRACT: Catalytic double hydrophosphination of inter-
24
catalysts. Among those, zirconium catalysts have been par-
nal alkynes and primary phosphines is possible using a zirco-
25-26
5
ticularly successful with primary phosphine substates,
nium
complex,
[κ -N,N,N,N,C-
providing substantial, albeit not ideal, conversions with even
unactivated alkenes—a substrate class all but untouched by
intermolecular hydrophosphination (Eq 2).
(
Me SiNCH CH ) NCH CH NSiMe CH]Zr (1). The reaction
3
2
2
2
2
2
2
proceeds via stepwise hydrophosphination to give vinyl
phosphine products, which can be isolated or further con-
verted to the respective 1,2-bis(phosphino)ethane (i.e., dou-
ble hydrophosphination). The catalysis is highly selective for
formation of secondary phosphine products.
Keywords: Hydrophosphination, double hydrophos-
phination, primary phosphine, zirconium, internal al-
kynes, acetylene
(2)
Investigation of zirconium-catalyzed intermolecular hy-
drophosphination of alkynes has yielded unique reactivity.
([κ -N,N,N,N,C-
CH]Zr) has good reactivi-
ty for the intermolecular hydrophosphination and double
hydrophosphination of internal alkynes, a category of sub-
5
1
-10
The
(Me
zirconium
SiNCH CH NCH
compound
CH NSiMe
1
Despite advances in selective P–C bond formation, sig-
1
1
3
2
)
2
2
2
2
2
nificant hurdles remain. Metal-catalyzed hydrophosphina-
tion has been under scrutiny for more than 25 years owing to
its potential to address challenges in the selective synthesis
of materials, biomolecules, and ligands for catalysis. Sub-
strates remain a particular challenge in metal-catalyzed hy-
drophosphination. For example, there are only a limited set
of metal catalysts that engage in the hydrophosphination of
alkynes, despite the greater reactivity of these molecules over
1
2, 17
21
strates not successful for Nakazawa
or Di Giuseppe et al.,
suggesting these are highly complementary systems. The net
result is that these catalysts now avail the full suite of alkyne
substrates for hydrophosphination and double hydrophos-
phination.
1
2-20
Treatment of alkyne substrate with two equivalents of
PhPH and 5 mol % of 1 results in hydrophosphination to
alkenes.
simple iron catalyst for the intermolecular double hydro-
Among those reactions, Nakazawa’s reports of a
2
1
2, 17
give the vinyl phosphine product after 15 h at 80 °C under
irradiation by an 830 lumen, 9-Watt LED lamp (Table 1).
Light is important for catalysis. Reactions run under ambient
light proceeded with consistent conversions, whereas reac-
tion run in the absence of light resulted in no hydrophos-
phination under identical conditions. Thus, direct irradiation
with visible photons appears to be necessary to activate al-
kyne substrates. The product phosphines are formed as a
mixture of E and Z isomers and can be isolated in yields up to
78%. Vinyl phosphine 2d and 2h are stable for at least 14 d at
ambient temperature under a nitrogen atmosphere. Hydro-
phosphination in the absence of 1 under otherwise identical
conditions fails to provide detectable amounts of hydrophos-
phination products.
phosphination of terminal alkynes stands out (Eq 1).
That
unique chemistry provided direct access to 1,2-
bis(diphosphino)ethanes, privileged architectures for late
transition-metal catalysis. This iron catalysis and a recent
report from Di Giuseppe et al. are the two known metal-
12, 17, 21
catalyzed double hydrophosphination reactions to date.
(1)
There are challenges with the phosphine substrate as well.
Primary phosphines have received limited attention as sub-
strates due to the potential for mixtures of secondary and
tertiary phosphine products, despite early successes with
Table 1: Hydrophosphination of internal alkynes
a
22-23
with PhPH2
these substrates.
In recent years, primary phosphines
have been under more intense reinvestigation due to the
potential to further functionalize the secondary phosphine
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ambient temperature with a 15.5 : 1 selectivity for the Z iso-
1
2
3
4
5
6
7
8
9
1
1
1
1
1
1
1
1
1
1
2
2
2
2
2
2
2
2
2
2
3
3
3
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3
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3
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mer. Experiments in which only one equivalent of PhPH was
2
added to bis(diethylamido)acetylene to purposely form the
single hydrophosphination products resulted in a 78 : 1 for-
mation of the E : Z isomers (Table S1). Unlike the other vinyl
phosphines (Table 1), these (2j E & Z) products readily isom-
erized in the presence of excess primary phosphine. Control
experiments indicated that 1 is not responsible for isomeriza-
tion (see Supporting Information for details).
NMR conv.
(%)
E:Z
ratio
entry
alkyne substrate
2a
99 (78)
99
5.1 : 1
1.9 : 1
1.8 : 1
3.1 : 1
3.7 : 1
Table 2: Double hydrophosphination of internal al-
a
0
1
2
3
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1
2
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0
1
2
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0
kynes with PhPH2
2b
2c
96
2d
89 (64)
75
entry
3a
alkyne
t/d
9 (62)
3 (71)
6
NMR conv. (%)
2e
78
92
88
96
78
73
2f
96 (76)
88 (70)
59 (41)
3.5 : 1
1 : 1.5
1 : 1.8
3b
2g
3c
2h
3d
4
3e
4 (55)
7
2i
46
80
1 : 1.2
b
3f
2j
15.5 : 1
a
Reactions run in a PTFE-valved NMR tube, heated to 80 °C
a
Reactions run in a PTFE-valved NMR tube, heated to 80 °C
under visible irradiation. Conversion to product phosphines
determined by P NMR integration. Values in parenthesis
under visible irradiation. Conversion to product phosphines
31
determined by P NMR integration.
31
b
represent isolated yields. Reaction ran at ambient tempera-
Treatment of a vinyl phosphine product with a second
equivalent of PhPH2 provides the corresponding 1,2-
bis(phosphino)ethane as a mixture of rac and meso isomers
ture.
Hydrophosphination
of
unsymmetrical
aryl/alkyl-
31
in high yields with P NMR chemical shifts in the range of –
substituted alkynes provides the secondary phosphine prod-
ucts with complete selectivity for the new P–C bond at the
alkyl-substituted position (i.e., R = alkyl and R’ = aryl in the
equation with Table 1) and no detectable amounts of P–C
bond formation at the aryl-substituted position (Table 1, 2a–
2c, 2i). The observed selectivity may be governed by steric
effects because the alkyl substituents employed are limited in
size. Indeed, hydrophosphination of diarylacetylenes pro-
ceeded smoothly, indicating that the reaction is not in some
way limited by an aromatic substituent (Table 1, 2d and 2e).
28 to –41 ppm. The reaction proceeds with regioselective
addition of the P–H bond across the alkyne such that no
formation of the 1,1 addition product is observed. Notably,
the second hydrophosphination product can be obtained
either by reaction of the isolated vinyl phosphine or in a one-
pot procedure by reacting alkyne with two equivalents of the
primary phosphine.
Unactivated alkynes are a challenging class of hydrophos-
phination substrates. However, these are converted by 1 to
both the single hydrophosphination products (vide supra)
and double hydrophosphination products (Table 2, 3d-3f).
The TONs for these unactivated substrates (TON = 14–19) are
nearly identical to the TON of aryl alkynes (TON = 15–18),
suggesting that unactivated substrates are no less efficient
than their activated counterparts. This similarity may repre-
sent inhibition only by steric factors as hydrophosphination
of diphenylacetylene had both a lower TON and TOF (TOF =
Unactivated alkynes react readily to provide the corre-
sponding vinyl phosphines (Table 1, 2f–2h). Hydrophos-
phination of 2-butyne provides the greatest conversion under
these conditions as compared to related dialkyl-substituted
alkynes, which demonstrates a steric dependence. The longer
chain alkyls also favored the Z isomer, which may be an ex-
pression of the decrease in steric hindrance of alkyl groups
interacting on the same side of the molecule. Alkynes pos-
sessing aryl groups favor the E isomer likely due to a de-
creased steric interaction between the phenylphosphino
group and the aryl substituent.
–1
8.7 d ) than all other internal alkynes tested (TOF = 10.4–
–1
30.7 d ). The observation that hydrophosphination catalysis
with 1 has comparable activity for both activated and unacti-
vated alkynes represents a rare exception in this field.
The
highest
selectivity
was
observed
for
Although double hydrophosphination of terminal alkynes
bis(diethylamino)acetylene (Table 1, 2j), which readily pro-
vided the single hydrophosphination products after 15 h at
12, 17, 21
has been demonstrated,
those substrates were not com-
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patible with 1. Attempted hydrophosphination of 1-hexyne
under an 1 atm of acetylene results in 65% yield of 1,2-
bis(phenylphosphino)ethane after 18 h (Eq. 4).
3
5
1
2
3
4
5
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7
8
9
1
1
1
1
1
1
1
1
1
1
2
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2
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2
2
2
2
2
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5
5
5
6
with 5 mol % 1 provided 5% conversion after 8 d at 80 °C
with a loss of anti-Markovnikov selectivity. Control reactions
without 1 provide virtually identical results, indicating that
this reaction is a thermal process rather than a catalytic one.
Previous investigation of heterofuctionalization using 1 as
(
4)
a catalyst with terminal alkynes were successful with diphe-
27-28
nylphosphine and diphenylarsine.
In those reactions, it
Removal of 1 by filtration through Celite® followed by dis-
tillation affords the product as a 1:1 mixture of rac and meso
isomers. Control experiments in which PhPH is heated un-
der acetylene gas in the absence of 1 fails to convert
measureable amounts of 1,2-bis(phenylphosphino)ethane
under identical conditions. It should be noted that the quali-
ty of the acetylene gas is crucial for hydrophosphination to
occur, as acetylene samples of lesser purity failed to provide
detectable hydrophosphination products.
was established that phenylacetylene inhibited catalysis such
that extended reaction times at relatively high temperatures
were required. Treatment of one equivalent of phenylacety-
2
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lene with two equivalents of PhPH in the presence of 1 pro-
2
vided 26% conversion to the single hydrophosphination
product 4 after four days at 100 °C (eq. 3). Extended reaction
times failed to deliver the second hydrophosphination prod-
uct
and
provided
the
hydrogenation
product,
PhCH CH PHPh (5), in 30 % conversion instead. Product 5 is
2
2
Conversion
of
acetylene
to
1,2-
the known hydrophosphination product of styrene with
35
25
bis(phenylphosphino)ethane was surprising based on the
lack of catalytic reactivity with terminal alkynes. It was antic-
ipated that acetylene would readily ring open 1 and form an
alkynyl compound related to those known for terminal al-
PhPH2.
27, 29
kynes,
a risk that seemed amplified by acetylene’s ability
to act as a bridging ligand between two zirconium centers.
Indeed, reaction of 1 with 1 atm of acetylene results in imme-
diate formation of bimetallic 6, in which acetylene bridges
the two zirconium centers (Eq 5).
(3)
Attempted hydrophosphination catalysis of phenylacety-
lene with 1 at these high temperatures and extended reaction
times gives, as anticipated, competitive dehydrocoupling of
3
1
1
the primary phosphine. Analysis of the crude P{ H} NMR
spectrum after seven days revealed a 20% conversion of
29
PhPH to dehydrocoupled products, allowing for a buildup
2
of hydrogen gas in the sealed NMR tube. Thus, it is hypothe-
sized that 5 arises from the hydrogenation of 4 by 1 or hydro-
genation of phenylacetylene to styrene with this ambient
hydrogen atmosphere. It has, however, been demonstrated
that 1 is a poor hydrogenation catalyst with a hydrogen at-
mosphere, though such forcing conditions were not explored
(5)
13
3
0
Compound 6 displays four resonances in the C NMR
spectrum, including a single alkyne peak at δ 94.2, indicating
a symmetric complex. Sublimation returns 6 as an off-white
solid, which is highly related to terminal alkynyl derivatives
in those studies. A related hydrophosphination system also
suffered from competitive hydrogenation during catalytic
21
hydrophosphination of phenylacetylene. Attempts to isolate
the vinyl phosphine intermediate by vacuum distillation
were hindered by the similar volatilities of both the vinyl and
saturated phosphines. Isolation of 5 by vacuum distillation
provided identical spectroscopic data as that for the authen-
27, 29
by conventional spectroscopic interrogation.
Treatment
of 6 with one equivalent of PhPH results in no detectable
ligand exchange after two days at 80 °C, which is similar to
the lethargic reactivity of (N N)ZrC≡CPh toward Ph PH, de-
3 2
spite the fact that both (N N)ZrC≡CPh and 1 are active cata-
2
25, 31
tic compound.
3
Nakazawa’s iron catalyst that successfully engages in dou-
ble hydrophosphination of terminal aryl alkynes has not
been demonstrated to be effective with internal alkyne sub-
lysts for the hydrophosphination of phenylacetylene with
29
Ph PH.
2
1
2, 17
In summary, we have reported the first example of a dou-
ble hydrophosphination of internal alkynes in a simple, one-
pot procedure. This is also the first example of a double hy-
drophosphination of alkynes to use a primary phosphine and
a rare example of a hydrophosphination of internal alkynes.
Acetylene gas was also shown to undergo hydrophosphina-
strates.
In this regard, compound 1 and CpFeMe(CO)2
represent a highly complementary pair of catalysts in this
exceedingly rare double hydrophosphination reaction. Dou-
ble hydrophosphination with terminal alkynes were also not-
21
ed in Oro’s report.
3
2-34
25
Secondary phosphines,
and primary phosphines have
tion with
1
to provide the common moiety 1,2-
been known to undergo hydrophosphination with ethylene,
but so far there has been no report of hydrophosphination
reactions involving acetylene. However, functionalization of
the parent molecule offers an unparalleled opportunity for
further synthesis of specialized diphosphines that are em-
ployed in an array of conventional transformations. Heating
bis(phosphino)ethane. Hydrophosphination of acetylene,
also a unique substrate, by 1 results in the formation of 6, a
bimetallic zirconium species. These double hydrophosphina-
tion reactions provide a significant complement to the only
other known catalysts for this reaction, Nakazawa’s iron
and a rhodium N-heterocyclic carbene com-
pound that afford similar reactivity with terminal alkynes.
The zirconium-catalyzed reactions occur in a stepwise fash-
1
2, 17
compounds,
21
a solution of PhPH in toluene with catalytic amounts of 1
2
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Page 4 of 5
ion, which has allowed for the convenient isolation of a fami-
ly of vinyl phosphines. Further exploration of this catalysis is
currently underway.
14.
A.; Beletskaya, I. P. Russ. J. Org. Chem. 2002, 38, 1479-1484.
15. Kondoh, A.; Yorimitsu, H.; Oshima, K. J. Am. Chem.
Soc. 2007, 129, 4099-4104.
Kazankova, M. A.; Shulyupin, M. O.; Borisenko, A.
1
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AUTHOR INFORMATION
Corresponding Author
16.
Ohmiya, H.; Yorimitsu, H.; Oshima, K. Angew.
Chem., Int. Ed. 2005, 44, 2368-2370.
17.
Itazaki, M.; Katsube, S.; Kamitani, M.; Nakazawa, H.
rory.waterman@uvm.edu
Chem. Commun. 2016, 52, 3163-3166.
18.
19.
Notes
Hu, H.; Cui, C. Organometallics 2012, 31, 1208-1211.
Takaki, K.; Takeda, M.; Koshoji, G.; Shishido, T.;
The authors declare no competing financial interest.
Takehira, K. Tetrahedron Lett. 2001, 42, 6357-6360.
0. Douglass, M. R.; Stern, C. L.; Marks, T. J. J. Am.
Chem. Soc. 2001, 123, 10221-10238.
1. Di Giuseppe, A.; De Luca, R.; Castarlenas, R.; Perez-
Torrente, J. J. J.; Crucianelli, M.; Oro, L. A. Chem. Commun.
016, 52, 5554-5557.
2. Zhao, G.; Basuli, F.; Kilgore, U. J.; Fan, H.; Aneetha,
0
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ASSOCIATED CONTENT
Supporting Information
2
2
Experimental procedures and characterization data. This
material is available free of charge via the Internet at
http://pubs.acs.org.
2
2
H.; Huffman, J. C.; Wu, G.; Mindiola, D. J. J. Am. Chem. Soc.
2006, 128, 13575-13585.
23.
S.; Concolino, T. E.; Yap, G. P. A.; Incarvito, C. D.; Rheingold,
A. L. Organometallics 1999, 18, 5381-5394.
ACKNOWLEDGMENT
Wicht, D. K.; Kourkine, I. V.; Kovacik, I.; Glueck, D.
This work was supported by the U.S. National Science Foun-
dation (CHE- 1265608 and CHE- 1565658).
24.
0.1002/chem.201602749.
5. Ghebreab, M. B.; Bange, C. A.; Waterman, R. J. Am.
Chem. Soc. 2014, 136, 9240-9243.
6. Bange, C. A.; Ghebreab, M. B.; Mucha, N. T.; Ficks,
A. Higham, L.; Waterman, R. Dalton Trans. 2015, 45, 1863-
867.
7.
Bange, C. A.; Waterman, R. Chem. Eur. J. 2016, DOI:
1
REFERENCES
2
1.
Wauters, I.; Debrouwer, W.; Stevens, C. V. Beilstein
2
J. Org. Chem. 2014, 10, 1064-1096.
2.
Rosenberg, L. ACS Catal. 2013, 3, 2845-2855.
1
3.
Rodriguez-Ruiz, V.; Carlino, R.; Bezzenine-Lafollee,
2
Roering, A. J.; Maddox, A. F.; Elrod, L. T.; Chan, S.
S.; Gil, R.; Prim, D.; Schulz, E.; Hannedouche, J. Dalton
Trans. 2015, 44, 12029-12059.
M.; Ghebreab, M. B.; Donovan, K. L.; Davidson, J. J.; Hughes,
R. P.; Shalumova, T.; MacMillan, S. N.; Tanski, J. M.;
Waterman, R. Organometallics 2009, 28, 573-581.
4
.
Pullarkat, S. A.; Leung, P.-H. Top. Organomet.
Chem. 2013, 43, 145-166.
2
8.
Tanski, J. M.; Waterman, R. Dalton Trans. 2008, 4488-4498.
29. Roering, A. J.; Leshinski, S. E.; Chan, S. M.;
Roering, A. J.; Davidson, J. J.; MacMillan, S. N.;
5
.
Pullarkat, S. A. Synthesis 2016, 48, 493-503.
6
.
Koshti, V.; Gaikwad, S.; Chikkali, S. H. Coord. Chem.
Rev. 2014, 265, 52-73.
Shalumova, T.; MacMillan, S. N.; Tanski, J. M.; Waterman, R.
Organometallics 2010, 29, 2557-2565.
7.
Glueck, D. S. Top. Organomet. Chem. 2010, 31, 65-
100.
30.
Waterman, R. Organometallics 2015, 34, 4693-4699.
1. Obata, T.; Kobayashi, E.; Aoshima, S.; Furukawa, J.
Polym. J. 1993, 25, 1039-1048.
2. Geer, A. M.; Serrano, A. L.; de Bruin, B.; Ciriano, M.
A.; Tejel, C. Angew. Chem., Int. Ed. 2015, 54, 472-475.
3. Kawaoka, A. M.; Marks, T. J. J. Am. Chem. Soc. 2004,
26, 12764-12765.
4. Edwards, P. G.; Malik, K. M. A.; Ooi, L.-l.; Price, A. J.
Dalton Trans. 2006, 433-441.
5. Brooks, P.; Gallagher, M. J.; Sarroff, A. Aust. J.
Chem. 1987, 40, 1341-1351.
Erickson, K. A.; Stelmach, J. P. W.; Mucha, N. T.;
8.
Glueck, D. S. Chem. - Eur. J. 2008, 14, 7108-7117.
9
.
Delacroix, O.; Gaumont, A. C. Curr. Org. Chem.
3
2005, 9, 1851-1882.
10.
Davies, L. H.; Stewart, B.; Higham, L. J. Organomet.
3
Chem. 2014, 39, 51-71.
11.
Gladysz, J. A.; Bedford, R. B.; Fujita, M.; Gabbai, F.
3
P.; Goldberg, K. I.; Holland, P. L.; Kiplinger, J. L.; Krische, M.
J.; Louie, J.; Lu, C. C.; Norton, J. R.; Petrukhina, M. A.; Ren,
T.; Stahl, S. S.; Tilley, T. D.; Webster, C. E.; White, M. C.;
Whiteker, G. T. Organometallics 2014, 33, 1505-1527.
1
3
3
1
2.
J. Am. Chem. Soc. 2012, 134, 11932-11935.
3. Kazankova, M. A.; Efimova, I. V.; Kochetkov, A. N.;
Afanas'ev, V. V.; Beletskaya, I. P.; Dixneuf, P. H. Synlett 2001,
, 497-500.
Kamitani, M.; Itazaki, M.; Tamiya, C.; Nakazawa, H.
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