Rhodium-catalyzed annulation of ynamides with bifunctional arylboron reagents.
Gourdet, Benoit; Rudkin, Mairi E.; Lam, Hon Wai; Organic letters 12 (2010) 2554–2557; doi:10.1021/ol100769p

data_1502992
_publ_section_title
;
 Rhodium-catalyzed annulation of ynamides with bifunctional arylboron
 reagents.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2554
_journal_page_last               2557
_journal_paper_doi               10.1021/ol100769p
_journal_volume                  12
_journal_year                    2010
_chemical_compound_source        'Benoit Gourdet'
_chemical_formula_moiety         'C27 H32 Cl N O5 Si'
_chemical_formula_sum            'C27 H32 Cl N O5 Si'
_chemical_formula_weight         514.08
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                79.8174(18)
_cell_angle_beta                 85.4258(16)
_cell_angle_gamma                80.7897(18)
_cell_formula_units_Z            2
_cell_length_a                   9.27962(19)
_cell_length_b                   11.2690(3)
_cell_length_c                   12.7790(3)
_cell_measurement_reflns_used    22458
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.9914
_cell_measurement_theta_min      3.5160
_cell_volume                     1296.50(5)
_computing_molecular_graphics    Shelxp
_computing_publication_material  'Platon, encifer'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'Shelxs Sheldrick'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3147
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
  1 omega    0.00   27.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0664   37.0000  -90.0000 27

  2 omega  -71.00   38.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0664   77.0000 -150.0000 109

  3 omega  -73.00   39.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0664   77.0000  -30.0000 112

  4 omega  -72.00   39.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0664   77.0000   90.0000 111

  5 omega  107.00  174.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -150.0000 67

  6 omega   39.00   74.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -150.0000 35

  7 omega   85.00  110.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -96.0000   66.0000 25

  8 omega  101.00  129.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  111.0000   60.0000 28

  9 omega   46.00   75.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -180.0000 29

 10 omega  142.00  168.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  111.0000   60.0000 26

 11 omega   43.00   76.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   90.0000 33

 12 omega   49.00   77.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -60.0000 28

 13 omega   39.00   65.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  120.0000 26

 14 omega  107.00  137.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  120.0000 30

 15 omega  100.00  126.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  179.0000   30.0000 26

 16 omega   38.00   76.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   60.0000 38

 17 omega   39.00   73.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -30.0000 34

 18 omega   93.00  119.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -122.0000  -62.0000 26

 19 omega   32.00  170.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000 -150.0000 138

 20 omega  105.00  177.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  111.0000   90.0000 72

 21 omega  105.00  138.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  111.0000 -150.0000 33

 22 omega  153.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  111.0000 -150.0000 25

 23 omega   39.00   65.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  150.0000 26

 24 omega   38.00   70.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  150.0000 32

 25 omega  106.00  150.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  179.0000  -90.0000 44

 26 omega   82.00  129.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  179.0000  120.0000 47

 27 omega   85.00  115.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -122.0000  -18.0000 30

 28 omega   67.00   93.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -116.0000   15.0000 26

 29 omega   66.00   98.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000   90.0000 32

 30 omega  114.00  139.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000   90.0000 25

 31 omega   46.00   72.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   30.0000 26

 32 omega  136.00  169.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -60.0000 33

 33 omega  122.00  147.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  150.0000 25

 34 omega  142.00  168.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  150.0000 -179.0000 26

 35 omega   31.00   68.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -96.0000   66.0000 37

 36 omega   82.00  134.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -150.0000  -44.0000 52

 37 omega   82.00  117.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -114.0000   36.0000 35

 38 omega -119.00   -6.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0664  -77.0000    0.0000 113

 39 omega -116.00  -14.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0664  -37.0000  120.0000 102

 40 omega -119.00   -6.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0664  -77.0000 -120.0000 113

 41 omega -116.00  -14.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0664  -37.0000    0.0000 102

 42 omega -116.00  -14.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0664  -37.0000 -120.0000 102

 43 omega -119.00   -6.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0664  -77.0000  120.0000 113

 44 omega   56.00  130.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0664  179.0000  120.0000 74

 45 omega -140.00  -28.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  -30.0000 112

 46 omega -140.00  -28.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000 -120.0000 112

 47 omega -140.00  -28.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000   60.0000 112

 48 omega -140.00  -28.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000 -180.0000 112

 49 omega   38.00   77.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -90.0000 39

 50 omega   79.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   30.0000 99

 51 omega   79.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -180.0000 99

 52 omega   79.00  166.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -90.0000 87

 53 omega   52.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000  150.0000 126

 54 omega   85.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  150.0000 93

 55 omega   79.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -30.0000 99

 56 omega   85.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -90.0000 93

 57 omega   79.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -150.0000 99

 58 omega   52.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000   30.0000 126

;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_sigmaI/netI    0.0191
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            27430
_diffrn_reflns_theta_full        76.18
_diffrn_reflns_theta_max         76.18
_diffrn_reflns_theta_min         3.52
_exptl_absorpt_coefficient_mu    2.060
_exptl_absorpt_correction_T_max  0.89
_exptl_absorpt_correction_T_min  0.7434
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_recrystallization_method
'slow evaporation of DCM/heptane solution'
_exptl_crystal_size_max          0.1690
_exptl_crystal_size_mid          0.1439
_exptl_crystal_size_min          0.0558
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         5388
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0787P)^2^+0.4750P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1142
_refine_ls_wR_factor_ref         0.1157
_reflns_number_gt                5059
_reflns_number_total             5388
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol100769p_si_003.cif
_cod_data_source_block           hl0001
_cod_original_cell_volume        1296.51(5)
_cod_database_code               1502992