Palladium-Catalyzed Alkynylation of Secondary α-Bromo Carbonyl Compounds via Stille Coupling
Jun Yong Kang; Brian T. Connell; Journal of Organic Chemistry 76 (2011) 6856–6859; doi:10.1021/jo200939u

data_4026512
_publ_section_title
;
 Palladium-Catalyzed Alkynylation of Secondary \a-Bromo Carbonyl Compounds
 via Stille Coupling
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6856
_journal_page_last               6859
_journal_paper_doi               10.1021/jo200939u
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C17 H21 N O2'
_chemical_formula_weight         271.35
_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                89.195(19)
_cell_angle_beta                 84.673(18)
_cell_angle_gamma                76.599(17)
_cell_formula_units_Z            2
_cell_length_a                   5.324(8)
_cell_length_b                   10.365(15)
_cell_length_c                   14.32(2)
_cell_measurement_reflns_used    991
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      27.31
_cell_measurement_theta_min      2.48
_cell_volume                     765.4(19)
_computing_cell_refinement
; 
  APEX-II (BRUKER-NONIUS, 2003) 
;
_computing_data_collection       'SMART (BRUKER-NONIUS, 2003)'
_computing_data_reduction        APEX-II
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'SMART CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_sigmaI/netI    0.0334
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7615
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         1.43
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9715
_exptl_absorpt_correction_T_min  0.9555
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2006)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.040
_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     194
_refine_ls_number_reflns         3402
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0422
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0578P)^2^+0.1462P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1182
_reflns_number_gt                2793
_reflns_number_total             3402
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200939u_si_002.cif
_cod_data_source_block           brcb190m
_cod_original_cell_volume        765.3(19)
_cod_database_code               4026512